2 day Chicago Itinerary
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2 day Chicago itinerary for the Weekend

Planning to Visit the Windy City but short on time? Fear not! With just 48 hours, you can experience the best of Chicago’s iconic sights, world-class museums, and delicious deep-dish pizza. This 2-day Chicago Itinerary is packed with must-see attractions, Museums, and iconic landmarks, all while leaving room for exploring hidden gems and indulging in Chicago’s legendary food scene.

Located on Lake Michigan in Illinois, Chicago is one of the largest cities in the USA and is popularly known as a “windy city”. Famed for its bold architecture, the city is dotted with so many skyscrapers like New York! Being an architecture lover and foodie, this trip was one of my best trips in the USA.

In just 2 days in Chicago, you can have deep-dish pizza, visit skyscraper viewing decks, go on a scenic river cruise, enjoy great pubs, and visit the world’s top art museums.

We booked flights for one weekend in April from Atlanta, just a short weekend trip! We fully explored the Chicago sights for whole 2 days! I would say, you can experience the best of Chicago in 2 days during the weekend, but if you want to stay longer it’s perfectly fine! I will include more options in this post! So keep reading!

Before I go deep into how to spend 2 days in Chicago, let me share a few important travel information when visiting Chicago.

Travel Tips to Visit Chicago in 2 Days

What’s the best month to visit Chicago, Illinois?

Spring season from March end to May is the best time to visit Chicago. Weather remains mild and you can enjoy blooming tulips and flowers all around the city! Also, the crowd will be fewer. You can see painting the Chicago River with green on St Patrick’s Day!

Another best time to visit Chicago is the Fall September to November. You can enjoy fall festivities and Halloween celebrations in the city, and the weather remains cool and comfortable.

Summer months from June to August are the peak tourist season in Chicago. So expect larger crowds and higher hotel rates! But this is perfect for outdoor events, festivals, and lakefront activities.

Winter from December to February is very harsh in Chicago and if you hate winters like me, avoid this time when Planning your Chicago trip! If you’re visiting it during the winter months, be prepared for cold weather and potential travel delays due to snow.

Overall, Late spring (May) and early fall (September) offer pleasant weather, fewer crowds, and a variety of activities, making it the best time to visit Chicago, Illinois.

Is 2 days enough for Chicago?

Certainly, you can cover most of the Chicago highlights and attractions in 2 days. From River cruises, architecture, museums, and Lakefront areas, you can cover major sightseeing places in Chicago in two days. With that said, as Chicago has so much to offer, it’s a good idea to plan your itinerary well in advance to make the most of your time. Make restaurant reservations and book tickets for popular attractions in advance to avoid long waits!

What’s the best way to get to Chicago? 

The city has two airports, Midway International Airport (MDW) and O’Hare International Airport (ORD). You can also easily reach Chicago by train from the airport to downtown. The Blue Line connects O’Hare Airport to downtown, and the Orange Line connects Midway Airport to downtown.

You can also catch an Amtrak that serves a few routes from various cities across the U.S.

How to Get Around for 2 Days in Chicago?

Getting around Chicago is relatively easy, thanks to its extensive public transportation system, walkable neighborhoods, and various transportation options! Chicago Transit Authority (CTA) operates an extensive network of buses and subway trains!

Chicago’s elevated train system, known as the ‘L’ train, is a convenient way to get around the city. It has eight lines (Red, Blue, Brown, Green, Orange, Purple, Pink, and Yellow) that connect various neighborhoods and suburbs all over the city.

how to get around for 2 days Chicago itinerary

The single-ride fare is $2.50 and 1 day Pass fare is $5. If you have more than 2 days in the city, you can buy a 3-day Pass for unlimited daily rides! Use a Ventra card for payments, which can be purchased at vending machines in train stations!

And the good thing is, the same VENTRA Card works on Buses. You can hop on buses and trains whenever needed! Lastly, Uber is always an option if needed.

Chicago is a very walkable city and many of Chicago’s attractions are within walking distance of each other, especially in neighborhoods like the Loop, River North, and the Near North Side. You can walk the scenic routes, particularly along the Chicago Riverwalk and Lakefront Trail.

Of course, if you’d prefer not to walk, you can also opt for a Hop on Hop off bus tour.

Another cool way to get around Chicago, especially around the river is Chicago Water Taxi. It connects popular spots like Chinatown, the Loop, and Michigan Avenue. Also, Shoreline Water Taxi runs seasonally between Navy Pier, Museum Campus, and other waterfront attractions.

Lastly, Hiring a car is not required for your 2-day Chicago itinerary. Street Parking is limited and Parking lots are very expensive in the downtown!

Quick Overview of 2-day Chicago Itinerary

My suggested two-day Chicago itinerary covers the city’s top sights and attractions. This includes the main highlights of the city and visiting its most famous attractions and museums.

Day 1: Chicago Theatre, Art Institute of Chicago, Millennium Park and The Bean, Architecture Boat Tour on the Chicago River, Navy Pier & Sunset views, Deep Dish Pizza.

Day 2: Skyscraper Viewing Decks, Museum Campus, explore a neighborhood, or visit Lincoln Park & Sunset at North Avenue Beach.

How to Spend 2 Days in Chicago: Itinerary

The two days in Chicago will be packed with lots of things to do and activities! Many sights are near each other, so you can cover lots of ground on foot!

Day 1 of 2 day Chicago Itinerary

8 AM: Breakfast at Goddess and the Baker

Grabbing a bite to eat at the Goddess and the Baker is the perfect way to start your first day in Chicago. It’s famous for its great American breakfast and coffee!

They have a wide selection of breakfast options including yogurt parfait, omelets, bagels, and waffles so you won’t have a problem finding something to your taste here.

There are multiple locations for Goddess and the Baker in the city, but visiting the location across Millenium Park is very convenient as your next stops are located along the way!

9 AM: Chicago Theatre

After fueling yourself, walk a few blocks to Chicago Theatre. This is a must-see attraction in Chicago. If you have time, definitely catch a show here in the evening. We booked our flights on a whim, so we didn’t get a chance to see any!

The Chicago Theatre was constructed in 1921 and designed by Cornelius Ward Rapp and George L. Rapp. It was the first lavish movie palace in the United States and was incredibly successful.  This led to the owners (Balaban & Watz) constructing other theaters of its design throughout America. And you can see the Lobby, how the design of the theatre is based on luxury!

I’d recommend catching a show here to experience this beautiful building. You can spend an evening watching comedy shows, live music performances, and theater productions.

However, if you don’t have time then simply head inside and go on a tour to see the luxurious architecture!

9:30 AM : Millenium Park and the Bean

After Visiting the Theatre, head to the most popular landmark in Chicago– Millenium Park. The Park is large and very beautiful. We visited during the Spring and there were so many flower blooms in the Park, with skylines in the backdrop.

Popularly known as “The Bean” (Cloud Gate), is the most famous piece of art in the park and a Popular icon of Chicago. This Public sculpture was designed by British artist Anish Kapoor, made up of 168 stainless steel plates!

Most popular attractions to visit in 2 days in Chicago

You can walk around the sculpture, take photos, and even go underneath it. You can see the stunning reflection of Chicago Skylines on Bean which makes it a popular location for Photography!

Being the most Photographic place to visit in Chicago, it remains jam-packed and crowded as this is one of the most popular things to do in Chicago! Visit it early in the day to get photos without crowds!

After this, make sure to walk around the Millennium Park. There’s plenty to see and do here including visiting the Lurie Garden(2.5-acre public garden), and Crown Fountain which is a work of art in itself!

If you’re coming to Chicago in the winter, you can even go ice skating on a temporary ice rink in Millennium Park!

10 AM: Art Institute of Chicago

The Art Institute of Chicago is a renowned and popular attraction in Chicago. With a million square feet of Space, it’s one of the world’s largest and oldest Art Museums and second to New York‘s MET in the USA. This Museum will present you with so many “wow” moments!

Aside from its ever-changing exhibitions, the museum has a permanent collection of around 300,000 art pieces from different cultures and periods around the world!

Chicago Art Institue

Wander through the grand halls and immerse yourself in the masterpieces of all the greats, like Van Gogh, Monet, and Picasso. Marvel at the famous paintings and learn the stories behind each piece. This is a must-visit landmark in your 2 day Chicago Itinerary.

The Art Institute of Chicago remains closed on Tuesdays and Wednesdays. Otherwise, it’s open between 11 AM to 5 PM, from Thursday to Monday and general admission costs USD 25 per person. Book your tickets here.

As you’re short on time, I recommend taking a guided tour of the museum to cover the main highlights and get to know more about the art you are seeing! I suggest not to skip this place from your 2-day Chicago Itinerary!

11 AM: Architecture Walking Tour

Chicago is home to some iconic buildings and impressive architecture. I planned my Chicago Itinerary in a way that I can see most of the beautiful architecture of Chicago in 2 days! Most of the buildings in the city are free to visit and many of them are within walking distance of each other.

You can also take the self-guided tour yourself if running out of time! First, visit the Palmer House – a Hilton Hotel. Built-in the 1920s, the stunning architecture reflects the luxurious Classical detailing of the French Beaux-Art Deco design!

2 day Chicago weekend itinerary

In the 19th century, the Palmer House was the city’s first hotel with elevators and the first hotel with electric light bulbs and telephones in the guest rooms! Also, the world-famous Chocolate Brownie is invented at this hotel! so must try it when here!

Next stop at the Rookery Building. Esteemed as an architectural marvel, designed by Burnham and Root in 1888, with a breathtaking lobby. This building blends Romanian and Moorish styles, with intricate ironwork and the iconic oriel staircase. Note that, it remains closed on Sunday!

The third stop on this list is La Salle Street & Chicago Board of Trading Building. Visit the iconic and historic towering skyscrapers on La Salle Street that tell the story of the city’s rich financial and architectural history! This was my favorite street, also we stayed at the hotel on this street just across the Chicago Board of Trading!

You can also visit the nearby Chicago Federal Reserve Building, the Monadnock Building(once the largest office building in the world), the Sullivan Centre, and Macy’s (Marshall Field & Company). You can book this 2 hour Chicago Architecture Walking Tour to learn more about the history of the city’s stunning architecture!

Lunch: Beatnik on the River

It might be Noon, once you finish all the sightseeing! Head to Riverside for the lunch. If you’re looking for drinks and good food, head to the Beatnik on the River.

The restaurant is spacious and the architecture is beautiful. The decor of the restaurant is Mediterranean-themed and attractive, perfect for the romantic setting by the river! The food was also good but I found the portions very small. But overall service was good.

1:30 PM: Chicago Riverwalk

After the Lunch, make your way to the Chicago Riverwalk. Chicago is built along a river, and the views are just gorgeous! It is a great way to take in the views of the city.

The Chicago Riverwalk is a 1.25 Miles Path, that starts from Lake Street and runs along the Chicago River until it reaches Lake Michigan. 

Along the way, you’ll get to see a variety of Murals, sculptures, cafes and so many bridges and overlooks for great views of the Chicago of architecture. Take your time and enjoy the walking path. 

However, the highlights of the Chicago Riverwalk are the iconic Wrigley Building and the DuSable Bridge. You can also stop by City Winery which offers delicious wine with the river views. With so much to offer, this riverwalk must be included in your 2 day Chicago itinerary! 

Afternoon: Chicago River Cruise — Must do for 2 days in Chicago

One of the most popular things to do in Chicago is to take an architecture River Cruise on the River. By this time, your feet will probably need a break from the constant walking, and this 90-minute river cruise is the perfect way to relax.

River Cruise is an excellent way to experience the legendary architecture of Chicago with the best seat on the cruise. All the cruises generally have a live narration with a guide. You will learn about some of the city’s best architecture and of course, the history of the city as you navigate through the heart of Chicago covering all 3 branches of the Chicago River.

2 day Chicago Itinerary

Most of the tours last for 60-90 minutes and offer full service on board as well as restrooms.

We took this Chicago Architecture Cruise. The tour lasted for more than 90 minutes! The guide was knowledgeable and it was a bit cheaper than other options I found online and at the wrecker drive near the Wrigley Building!

Evening: Sunset at Navy Pier

Wrap your first day in Chicago, and head out to Navy Pier. This 50-acre Pier is just a few blocks from the downtown Chicago area, at Lake Michigan. It is a must-visit and the most popular tourist attraction in the city with the best views of the city, gardens, rides, many shops, and restaurants!

You’ll find plenty of things to do here including Fairground rides, live music performances, and special events celebrations! The Pier itself offers the best skyline views of the city and Lake Michigan!

Navy Pier Chicago

Also, read this Fun fact – The Ferris Wheel was invented in Chicago. They created it for the World’s Fair in 1883. At first, they considered creating a larger version of the Eiffel Tower, but they wanted to be different! So a guy named George Ferris came up with the idea of a giant spinning wheel people could ride on.

So, one of the most unmissable things to do in the Navy Pier is going on a ride on the Centennial Wheel, which is a 200-foot tall Ferris Wheel. It’s cool to ride one where the Ferris Wheel was invented! From the top, you’ll be able to see amazing views of the Cityscape and beyond! It is a very popular attraction in Chicago, so purchase your ticket in advance.

Hours: Sunday – Thursday, 11:00 AM to 8:00 PM; Friday – Saturday, 11 AM to 9:00 PM. Also, Rides are seasonal, they don’t operate in the colder winter months.

Two days in Chicago

Pro-tip: Bars on Navy Pier offer alcoholic drinks to go. You can drink anywhere along the pier freely. Take advantage of this after our Ferris wheel ride while you walk around the Pier!

You can also browse the shops and boutiques at Navy Pier, where you can find souvenirs, gifts, apparel, jewelry, and more. You can also explore the Chicago Children’s Museum, which offers interactive exhibits and hands-on activities for kids of all ages.

Navy Pier hosts live music performances, street performers, and special events throughout the year. Check the schedule for concerts, festivals, and cultural celebrations during your visit.

Overall, Navy Pier is a fun place to visit in Chicago. It is free to visit but rides and other activities do have entry fees.

how to spend 2 days in Chicago

After exploring the Pier, head to nearby Milton Lee Olive Park. Watching the Sunset at Milton Lee Olive Park is the perfect way to end the first day of your 2 days in Chicago.

The Park is named after Milton Lee Olive, a Vietnam War Veteran. It is located on Lake Michigan and offers spectacular views, especially at sunset. You will also find plenty of walking paths along the Lake with Chicago Skylines views.

Dinner: Deep Dish Pizza at Gionardo’s

For Dinner, you can opt for restaurants and cafes at Navy Pier including food courts which offer plenty of options to suit your tastes. But I will suggest Giordano’s Deep Dish Pizza for dinner!

They have multiple locations throughout the city but you can choose the Navy Pier location, so you don’t have to go far for dinner! Make the reservations once you arrive at the Navy Pier, browse the Pier, and then have dinner!

Deep-dish pizza is a famous dish invented in Chicago. It’s more rich than your typical pizza and fills you up quickly. Giordano’s is home to the best deep-dish pizzas in all of Chicago, and you’ll find plenty of options!

We ordered super veggie Pizza, customized to our tastes! Also, must order their Garlic french fries, they are super delicious! This Chicago-style deep dish has cheese and typically the toppings are underneath a layer of sauce! But overall, I liked it so much! My mission for the trip was accomplished!

If you’re looking to see and taste the best of Chicago in 2 days, this is the restaurant you need to visit!

Day 2 of 2 Day Chicago Itinerary

It’s time for your second day in Chicago! Today you are going to take in some more Museums and sights in the city. Feel free to adjust this 2-day Chicago Itinerary according to your interests.

Today’s attractions are grouped into two areas of the City: the South Side and the North Side. You’ll need to hop on the Bus for a few stops!

Breakfast at Beatrix

For me, breakfast is the most important meal of the day! Start your 2nd day in Chicago with Breakfast at Beatrix or Wildberry Pancakes & Cafe. Both places have multiple locations throughout the city. Find one near to your Hotel or on the way to your next sightseeing spot!

Wildberry Pancakes is one of the best breakfast places in Chicago. The Pancakes are their specialty and you’ll be spoilt for your choices with different flavours!

If Pancakes aren’t your thing, another great option for breakfast is Beatrix. This restaurant focuses on healthier options with plenty of vegetarian and vegan options.

9 AM: Chicago Sky deck

Make sure you finish your breakfast early and reach Wills Tower by 9 AM! To truly make the most of your 2 days in Chicago, you need to visit Skydeck Chicago when you are here!

Located on the 103rd Floor in the Wills Tower, Skydeck Chicago offers breathtaking views of the city. The Wills Tower was completed in 1974, it was the World’s tallest building and it held its title for a good 25 years! But today still it is one of the highest observation decks in the United States.

You will get a bird’s eye view of the city with the area as far as 50 miles away! On a clear day, you can see four states from here, how cool isn’t it? But apart from views, there is so much to know here! On your way to the elevators, you’ll pass through a series of exhibits that tell a brief history and story about Chicago.

If you have daring, head out onto the “Ledge”. The ledge is made up of four glass view boxes and you’ll get an unobstructed view of Chicago. This will make you feel like floating right above the city! This is an excellent Photo opportunity and this experience is included in your ticket. But if you have a fear of heights, don’t attempt!

It is one of the most popular attractions in Chicago, I recommend visiting first thing in the morning when it opens! Remember, I said to be here at 9 AM and finish the breakfast early! It is also advisable to book your tickets in advance so you don’t waste time waiting in line. The Skydeck remains open year-round and usually opens at 8.30 AM or 9:00 AM.

There are several restaurants, cafes, and shops in the lower part of Wills Tower, known as Catalog. You can go for cold drinks or coffee after your visit.

11 AM: Grant Park and Museum Campus

After you’ve had your fill of the city skyline views make your way to Grant Park. This is also one of the best places to visit in Chicago in 2 days. The Park is huge and there is so much to do here. From gardens, and sculptures to Museums, there is something for everyone here!

Museum Campus Chicago

The most popular attraction in the Park is Buckingham Fountain. This iconic fountain is one of the largest in the world and uses approximately 15,000 gallons of water per minute! Sounds crazy! The fountain also performs a water show hourly so make sure to witness it.

Grant Park is also a great place for taking photos of the Chicago skyline from a distance. I visited during the spring and it was breathtaking with spring blossoms. This place was my favorite from our 2 days in Chicago.

Museum Campus Attractions

After exploring the Grant Park, head to the Museum Camus. This 57-acre park is home to some of the best museums in the city. So, immerse yourself in the city’s rich cultural scene through a visit to one or two world-renowned museums. The museums are large, and can easily take 2-3 hours, so choose one that interests you!

The area is known as Museum Campus just like the Museums in the National Mall of Washington DC. Here are a few top attractions to visit on the Campus.

If you’re visiting with the kids, definitely check out the Field Museum. This is the World’s largest natural history museum and is home to Sue, the largest and most complete Tyrannosaurus Rex (T-Rex) fossil ever found! You’ll also find exhibits covering animal, bird, and plant life from around the world!

Adults can appreciate the Shedd Aquarium, once the largest indoor aquarium in the world. It has an impressive collection of 32,000 animals and fascinating marine life such as sharks, penguins, beluga whales, and sea otters!

If you’re interested in Space and astronomy, visit Adler Planetarium, where you can embark on a cosmic journey through immersive exhibits and captivating shows. It was the first Planetarium in the USA and is also a National Historic Landmark.

Overall, there is so much to do and plenty to see here. The only thing is to note that it has limited opening hours so check the timings before your visit. Also, visiting all the attractions is pretty time-consuming, so choose one or two to include in your 2 day Chicago Itinerary, have a great time at the Museum Campus during your weekend trip!

Lunch: Portillo’s Hot Dog

After being in the South Side, head to the Chicago Downtown area for some actions. Chicago offers endless dining options but you need to try Portillo’s Hot Dogs during your 2 days in Chicago.

This Chicago-born chain is famous for its juicy hot dogs, tasty Burgers, and delicious Chocolate Cake. They have vegetarian hot dog options and I was happy about it! After lots of walking, this is the best way to refuel yourself. It can get very crowded during the day but has ample seating and space for people to relax.

3 PM: Walk the Magnificent Mile

Without a doubt, the Magnificent Mile is one of the most popular places to visit in Chicago. It is one of the most famous shopping destinations in the world. This upscale shopping district boasts an array of boutiques, department stores, luxury brands, and plenty of designer shops.

If you’re looking for Shopping, you’ll find everything from high-end stores to budget-friendly options. And when you need a break from Shopping, there are plenty of restaurants and cafes to choose from.

However apart from shopping, you can visit a few most popular attractions like the Wrigley Building, John Tribune Tower, Wings of Mexico Sculpture, and John Hancock Center.

Walk towards the North and make your way to the Starbucks Reserve Roastery. This is a must-visit for Coffee lovers like me! Starbucks Reserve Roastery, Chicago is home to a selection of the rarest and most extraordinary coffees on the earth!

Also, it is the largest Starbucks in the world with five floors covering over 35,000 sq ft area! They offer coffee flights, an on-site cafe, a rooftop deck, and delicious pastries. If you’re into Coffee, don’t miss this place in your 2 day Chicago Itinerary.

4 PM: Explore the Neighborhood OR Lincoln Park

Afternoon, make your way to the North Side and reach Lincoln Park Conservatory. I visited Chicago during the Spring, it was perfect to see the spring blossoms at the conservatory. The massive conservatory features several rooms showing off plants from around the world! The Conservatory is free to visit but you’ll need to book a time slot online.

After visiting the Conservatory, head to the Nature Boardwalk at Lincoln Park Zoo. This is a great spot to unwind and take a break from all the hustle and bustle of the city. There’s also a pond where you can spot turtles, ducks, and other wildlife.

One of the unmissable sights within the Nature Boardwalk is the Educational Pavilion which is one of the most unique things you’ll see during your 2 day Chicago itinerary.

Lincoln Park Conservatory Chicago

And lastly, if you’re visiting Chicago with kids, spend your time at the Lincoln Park Zoo. It’s one of the oldest zoos in the country and it’s completely free to visit! You will see exotic animals including giraffes, zebras, and Lions, with exhibits on sea creatures.

If you don’t wish to visit Lincoln Park and want to fully immerse yourself in the local culture, venture into vibrant neighborhoods of Chicago like Pilsen, Lakeview, or Wicker Park. 

Chicago is a city of diverse neighborhoods, each with distinct Charm, character, and attractions, offering trendy shops, art galleries, and a diverse culinary scene!

Pilsen: Pilsen is a vibrant area known for its rich Mexican heritage, colorful murals, and lively street art. Find lots of authentic Mexican cuisine here. A must-visit place for you here is the National Museum of Mexican Art, which features a diverse collection of Mexican art and artifacts.

Chinatown: Immerse yourself in the Chicago’s Chinatown. You can wander through the streets, visit the unique shops and markets, and savor authentic Chinese cuisine. Don’t forget to click photos at the beautiful Chinatown Square and its traditional Chinese architecture. 

Wicker Park: A trendy Chicago neighborhood known for its arts and music scene and nightlife, Wicker Park is a great place to visit right on the Blue Line train. You can visit numerous art galleries, trendy shops, chic restaurants, and classic Chicago stores like Reckless Records.

Evening: Sunset at North Avenue Beach/Visit the Rooftop Bar

There’s no better way to end your 2 days in Chicago than by admiring an epic sunset. Chicago has so many viewpoints to watch the sunset and North Avenue Beach is spectacular! 

It’s one of the city’s most popular beaches and is located within Lincoln Park so you won’t have to walk far after visiting the Zoo or the Nature Boardwalk. You’ll get breathtaking views from the beach house here at the sunset.  

Make sure to stay a bit longer after the sunset to see the city all lit up. It’s truly an incredible experience!

Best things to do in Chicago in 2 days

But if you want to end your day with cocktails in hand along with the best city views, head to one of the rooftop bars in Chicago. You can consider visiting the London House Rooftop or Godfrey Hotel Rooftop Bar which offers delicious cocktails with the Chicago skyline. You can also check out Speakeasy Bars in downtown Chicago.


For the Dinner today, head to Pizzeria UNO. This is the main conic pizzeria that invented Deep Dish Pizza in 1943! so, if you want to visit the deep dish pizza origin and history then, there is no better place than UNO!

Hands down they are the best in the city! You can either create your own Pizza here, or you can try one of their many tasty options including Veggie and famous Spinoccoli. They also serve a wide variety of pasta dishes, salads, sandwiches, and desserts.

There is no better way to end your 2 days in Chicago, than by dining here!

Other Options for 2 Days in Chicago

  • Chicago beaches: If your 2 days in Chicago happen to coincide with the sunny summer months, then head to the beach! With miles of sandy shores along Lake Michigan, take sunbathe, swim, or take a walk along the waterfront. Popular beaches include North Avenue Beach, Oak Street Beach, and Montrose Beach.
  • Bike on Lakeshore Trail: For cycling enthusiasts, the Lakeshore Trail provides a scenic route along Lake Michigan. Tourists can rent bikes and ride along the trail, enjoying views of the city skyline and the lake. The trail is well-maintained and offers a fun outdoor experience. You can book this Chicago Bike Tour that is highly booked!
  • Visit 360 Degree Chicago: Another option to View Chicago Skylines is 360-degree Chicago, found on the 94th floor of the building, just over 1,000 ft above street level. The viewing platform here is a particularly popular location to visit when it is dark, so you can see the city lights, although you get a great view of the city at any time of day of course. For an extra thrill, try the TILT experience – an enclosed moving platform that tilts 30 degrees out of the building from the 94th floor! Make sure to book your tickets in advance here.

Best Tours in Chicago

I enjoy taking walking tours when visiting a new city, and Chicago is no exception. Walking tours can be a great way to learn about the history of the city or an area, a specific attraction, or the local cuisine from a knowledgeable local guide. Here are some suggested options to check out for your 2-day Chicago Itinerary.

  • Hop on a Sunset Cruise to see the Chicago River with sunset colors and beautiful skylines at night!
  • Chicago is well known for its architecture. This guided tour of Chicago’s Secret architecture is an excellent way to learn more about the city & its architecture!
  • If you want to try many different foods and learn a bit about the history of Chicago, take a food walking tour. This food tour of Chicago’s culinary highlights includes pizza, hot dogs, and Italian beef sandwiches!
  • Chicago is also home to several impressive street art pieces. This guided tour of Chicago’s street art is a great introduction to the scene.
  • Chicago has a history, especially with prohibition and the Industrial Revolution so I highly recommend going on this gangsters and ghosts walking tour if you want to hear the interesting history of the city, the most famous gangsters, as well as some of the city’s more famous ghost stories!

If you do decide to take one or more of these tours, you may need to adjust this two-day Chicago Itinerary accordingly.

Where to Stay during Your 2 Days in Chicago

Chicago has endless neighborhoods within a city with a wide range of accommodation options for every budget. So this can be tough to decide to find the best area to stay in Chicago. Here are the most popular areas in Chicago:

  • Downtown Chicago/The Loop  – It’s Perfect for first-time visitors
  • Magnificent Mile – known for luxury stays and shopping
  • River North – the best place to stay for nightlife
  • Wicker Park – one of the coolest areas in Chicago
  • The Gold Coast – a beautiful area along Lake Michigan

You can consider staying in the Loop or River North neighborhoods. These areas provide easy access to major attractions and public transportation and minimum travel is required. That makes sense as you have only 2 days in Chicago!

Note that prices can vary dramatically depending on the time of year and if major events are happening during your visit. If you are flexible with your travel dates it is worth trying different dates to see if prices change.

We stayed at the Residence Inn Chicago Downtown/Loop, La Salle Street near the Chicago Board of Trading. The Hotel was at a convenient location, a 5-minute walk from the nearby train station. All the major sightseeing attractions are located nearby to it.

Our Room had a fully equipped kitchen with a stovetop, a dishwasher, a microwave, and a refrigerator. You can enjoy the complimentary breakfast with a variety of options. This hotel was perfect for our weekend in Chicago!

Here are my top recommendations for where to stay in Chicago across a variety of styles and budgets:


Langham Chicago — Just 2 blocks away from Magnificent Mile, this luxury hotel towers above the city in a skyscraper designed by renowned architect Mies van der Rohe, offering upscale amenities and stylish comfort in the heart of downtown Chicago.

Drake Hotel — A luxury hotel nestled near the northern end of the Magnificent Mile in the posh Gold Coast neighborhood, the Drake offers views of Lake Michigan, spacious rooms, and high-end dining options. It’s surrounded by ample luxurious shops and the beautiful Oak Street Beach.

Hyatt Regency Chicago – Located in the heart of downtown, in the bustling Loop district, Hyatt Regency offers proximity to major attractions. The hotel boasts modern rooms with cityscape views, on-site dining options, and a fitness center.

Mid Range

Hotel EMC2 Autograph Collection — Located on Chicago’s famous Magnificent Mile, this is a well-rated boutique hotel within easy walking distance of many attractions.

CitizenM Chicago Downtown – This is a well-rated and centrally located hotel offering good value private en-suite rooms at a decent price.

Congress Plaza Hotel — Directly across from Millennium Park and sitting on the iconic Michigan Avenue, Congress Plaza Hotel offers elegance, luxury, and history in the heart of downtown Chicago. This historic Chicago hotel offers stunning city and lake views, on-site dining options, and free WiFi.


Hotel Felix — One of the best budget options if you’re on a tight budget! Located in Chicago’s vibrant River North neighborhood, this eco-friendly hotel is within walking distance of the unique shops and top restaurants on the Magnificent Mile.

Ivy Boutique Hotel — This boutique hotel is located in the heart of downtown Chicago and offers spacious rooms with floor-to-ceiling windows and upscale amenities.

Of course, there are many more options. You can see lots more options for accommodation in Chicago, including apartments, hotels, hostels, and more, on booking.com here.

two day Chicago Itinerary

Is Chicago City Pass Worth for a 2-day Chicago Itinerary?

This will depend on what is your interests and which Chicago attractions you visit. The Chicago City Pass is useful and worth every penny if you visit 5 or more Chicago attractions! This will save lots of money!

If you look at the above Chicago Itinerary, you can cover most of the places with your Chicago City Pass. The Pass is valid for 9 days and makes sense to buy if you plan to visit major attractions in Chicago for your 2-day Chicago Itinerary!

FAQs about 2 days in Chicago: Itinerary

What is Chicago best known for?

Chicago is famous for its architecture, culture, and amazing food. Some of the many things Chicago is famous for are Chicago-style hot dogs, deep-dish pizza, jazz music, and 1920s gangsters! Of course, the city has amazing museums and towering architecture!

Is Chicago very walkable?

Chicago is a very walkable and pedestrian-friendly city. Most of the Chicago sightseeing attractions are near each other, making it easily accessible by foot or public transportation! You don’t need a car in Chicago.

Is it safe to visit Chicago? 

Generally, Chicago’s downtown and popular tourist areas like the Magnificent Mile, the Loop, and the Riverwalk are pretty safe. As with other tourist destinations take precautions when you walk around at night! Avoid dark alleys and low-lit areas at night!

How windy is it in Chicago? 

It’s pretty windy, especially in the winter and along Lake Michigan! The funny thing is that the nickname “Windy City” was not created as a reference to the weather, but rather to local politicians in the 1800s who blew a lot of hit air!

Is Chicago worth visiting?

Yes, Chicago is worth visiting. The City is one of the best places to visit in the USA. Chicago has a diverse culture, an amazing food scene, stunning high skyscrapers, and old-age architecture, and you can experience the best music shows.

This sums up 2 day Chicago Itinerary. Although it’s not enough and this is perfect reason to Return here! Hope this article helps! Share and save to read it Later.

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