Chicago in 2 Days: The Perfect Itinerary From a Local (2024)

What should you do if you’ve only got 2 days in Chicago? How about deep dish pizza, skyscraper viewing decks, river cruises, great brewpubs, and one of the world’s top art museums?

Chicago is one of the coolest places in the United States. That’s why I moved there and stayed for a decade! This local’s guide to the Windy City includes all the popular tourist attractions you’ll want to check out, plus some insider suggestions to help you truly experience Chicago.

chicago in 2 days

I’ll take you to iconic sights like Willis Tower, the Art Institute, and Wrigley Field, while also visiting dive bars, improv clubs, and smaller neighborhoods that aren’t listed on other Chicago guides. 

Two days in Chicago may not be enough to see everything, but it’s more than enough to get a taste of some of the city’s best museums, food experiences, tourist attractions, and cultural spots. Read on for my suggested 2-day itinerary!

LOCAL’S TIP: Cars are not required in Chicago, because the public transit system is solid. The CTA operates an extensive network of buses, plus the subway trains (“The L”) that travel all over the city. The subway connects the city directly with O’Hare and Midway Airports. I recommend buying a 3-day CTA pass, which provides unlimited rides. Uber is always an option if needed.

Quick Summary: 2-Day Chicago Itinerary
Day One:
Art Institute of Chicago
Millennium Park and The Bean
Architecture Boat Tour on the Chicago River
Deep Dish Pizza Lunch
Skyscraper Viewing Decks
Chicago Evening Activities: Sports or Live Music
Bar Hopping
Day Two:
Museum Campus
Food Walking Tour for lunch
Explore a Neighborhood: Pilsen, Lakeview, Wicker Park
Magnificent Mile Shopping and Dining
Catch an Improv Show

Chicago in 2 Days: Itinerary for Day 1

9 am: Art Institute of Chicago

Art Institute of Chicago

Start your adventure with a visit to the renowned Art Institute of Chicago, a world-class museum in Downtown Chicago that houses an extensive collection of art spanning different cultures and time periods.

Wander through the grand halls and immerse yourself in the masterpieces by all the greats, like Van Gogh, Monet, and Picasso. Marvel at the famous paintings and learn the stories behind each piece.

10:30 am: Millennium Park and The Bean

After exploring the Art Institute, take a stroll around Millennium Park and neighboring Grant Park. This is where the huge Lollapalooza music festival takes place every summer.

bean sculpture chicago

As you wander through this urban oasis, stop and admire the famous Cloud Gate sculpture, affectionately known as “The Bean.” Also check out Crown Fountain, which spits out water from a video screen, creating a cool visual effect.

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

12 pm: Architecture Boat Tour on the Chicago River

As the afternoon rolls in, embark on an Architecture Boat Tour along the majestic Chicago River. Relax and enjoy the views while cruising through the heart of the city, surrounded by architectural wonders that showcase Chicago’s rich history.

chicago winter river boat cruise
Any good itinerary for Chicago in 2 days must include the architecture boat tour!

Listen to stories and anecdotes from knowledgeable guides who bring the city’s skyline to life. The architecture river cruise is the #1 activity I recommend to friends when they visit me in Chicago, because it provides great views through the heart of Downtown and offers historical commentary to help you learn about the city.

1:30 pm: Deep Dish Pizza Lunch

No visit to Chicago would be complete without indulging in the city’s famous deep dish pizza. It’s so thick you have to eat it with a knife and fork!

deep dish pizza

Head to Giordano’s or Lou Malnati’s, two popular pizzerias, and treat your taste buds to Chicago-style deep dish. Be aware that deep dish takes at least 45 minutes to cook, so expect to be sitting in the restaurant for a while, or look for a place that allows you to order ahead.

LOCAL’S TIP: For some variety, join a Chicago pizza tour, which samples multiple pizza joints, including deep dish and thin-crust, and you won’t have to wait as long at each restaurant.

3:30 pm: Skyscraper Viewing Decks

Spend late afternoon enjoying breathtaking views from Willis Tower, formerly known as the Sears Tower. This was actually the tallest building in the world until the 1990s.

Ascend to the Skydeck and step onto “The Ledge,” a glass balcony that extends from the building, offering panoramic views of the magnificent cityscape below. 

willis tower skydeck

The main alternative to the Willis Tower is the John Hancock Center. This towering architectural marvel offers its own set of captivating views of Chicago.

Head to the 360 Chicago Observation Deck, where you can enjoy panoramic city views that stretch up to four states. For an extra thrill, try the TILT experience – an enclosed moving platform that tilts you out over the street from the 94th floor. 

LOCAL’S TIP: For years, the Signature Room on the 96th floor was the way to get the best views inside the Hancock Tower without having to pay for the observation deck. But sadly, Signature Room permanently closed in late 2023, so it’s no longer an option. Ignore any guides that tell you to go there.

6 pm: Find Dinner

Downtown and the surrounding West Loop, River North, and Old Town areas have a bunch of renowned restaurants. I’ll leave the decision up to you. Popular options include: 

Alinea: This three-Michelin-starred restaurant is one of the most sought-after dining experiences in the city. Alinea is known for its innovative and artful presentation of dishes, pushing the boundaries of modern gastronomy. 

The Girl & The Goat: Opened by ‘Top Chef’ winner Stephanie Izard in 2010, this West Loop hotspot remains one of the city’s most popular restaurants. The Girl & the Goat menu is centered around small plates, offering a wide range of flavors and ingredients inspired by global cuisines.

Gibsons Bar & Steakhouse: This classic Chicago institution is perfect for meat lovers. As the first restaurant in the city to offer USDA Prime Angus Beef, Gibsons has a reputation for serving some of the best steaks in town. The old-school ambiance, extensive wine list, and top-notch service make it a popular choice.

Portillo’s: For a more affordable meal, check out Portillo’s, a local institution. You’ll find all the famous Chicago food items here, like hot dogs and Italian beef sandwiches, at reasonable prices. The best part is the Chocolate Cake Shake. It’s a chocolate milkshake with big hunks of cake and swirls of icing throughout. It’s one of the most indulgent desserts I’ve ever had! 

portillos chicago
Inside Portillo’s, home of the cake shake.

7:30 pm: Chicago Evening Activities: Sports or Live Music

After dinner, decide which late-night activity you’d like. You can have several options. See my post on Things To Do in Chicago at Night for a more extensive list of suggestions.

If you’re a sports fan, try snagging tickets for a Cubs game at Wrigley Field. Consider a White Sox, Bulls, or Blackhawks game as a backup plan if Cubs tickets are too hard to come by. 

There are always live concerts happening in the city. From superstar acts performing in arenas to indie rock bands at local clubs, music fans will plenty of options. The Chicago Theatre, Rivera Theatre, Metro, and Vic Theatre are some of the most storied music venues in the city, so check their schedules to see who’s playing.

If you just want the “most touristy” evening activity, head to the Green Mill, the iconic jazz club Uptown. This place has been in business for more than 100 years. Al Capone used to be a regular.

green mill jazz musicians

They still have musicians playing old-time jazz music, with a dance floor. Many guests even dress up in old-fashioned outfits to capture the spirit of the era. The Green Mill has a unique atmosphere and is always a fun time. You can take the Red Line subway train there.

10 pm: Bar Hopping Options

For bar hopping, head to Wicker Park if you’re in your 20s, the Wrigleyville area if you want sports bars, or Boystown if you’re seeking an LGBTQ crowd. Drinks tend to be cheap in Chicago, and many spots are cash-only.

Karaoke fans should head straight for Alice’s Lounge, a dive bar in Avondale. Be warned that Alice’s gets crowded, so you may only get to sing once even if you stay all night.

If you’re really adventurous, head to the Wieners Circle in Lincoln Park on a Friday or Saturday night. This is the famous hot dog stand where the employees berate the customers, and the customers yell back. It’s all in good fun, and it’s a wild experience! 

LOCAL’S TIP: My former neighborhood of Logan Square has the best bars in Chicago. Options include the ultra-cool ’70s vibe of the Heavy Feather, hipster spots like Slippery Slope and Cole’s, arcade bars Emporium and Logan Arcade, trendy spots like Revolution Brewing, and dive bars like Whirlaway and Go Tavern. Get to Logan Square via the Blue Line train.

Chicago Day 2 Itinerary

9 am: All the Museums

Start your second day in Chicago by immersing yourself in the city’s rich cultural scene through a visit to some of its world-renowned museums.

The area known as “Museum Campus” houses three first-class facilities, which are among Chicago’s top tourist attractions.

chicago museum campus

Choose from the Field Museum, where you can delve into natural history and discover ancient artifacts; the Shedd Aquarium, where you can get up close and personal with fascinating marine life such as sharks, penguins, beluga whales, and sea otters; or the Adler Planetarium, where you can embark on a cosmic journey through immersive exhibits and captivating shows. Museum Campus is also a great place for taking photos of the Chicago skyline from a distance.

Other cool niche museums elsewhere in the city include the National Museum of Mexican Art in Pilsen, the Swedish American Museum, the Chicago History Museum (which has a cool exhibit on the Great Chicago Fire of 1871), the Museum of Illusions, and the quirky International Museum of Surgical Science.

For nature and wildlife lovers, consider the Garfield Park Conservatory or the Lincoln Park Zoo. The massive conservatory features several rooms showing off plants from around the world, while the zoo is completely free and open year-round. It’s known for its giraffes and polar bear.

lincoln park zoo

You won’t be able to visit all of these museums and attractions, so it’s best to pick a couple and take your time enjoying them, rather than rushing around to squeeze too many into your 2-day itinerary.

LOCAL’S TIP: I highly recommend picking up the Chicago Citypass, which provides admission to up to five of the city’s top tourist attractions. For one price, you can visit the Willis Tower Skydeck, the Art Institute, the Architecture River Tour, the Shedd Aquarium, and another museum of your choice. 

1 pm: Lunch

For lunch, try some of the other famous Chicago food experiences, such as a Chicago hot dog (don’t you dare put ketchup on it!) or an Italian beef sandwich.

Consider the Ultimate Food and Walking Tour, which takes guests to several eateries for samples of pizza, hot dogs, and pastries, plus visits to some of Downtown’s most interesting spots, like the Jay Pritzker Pavilion and the Chicago Theatre.

For a different culinary experience, take the Chinatown Food and Walking Tour to see the neighborhood’s best dim sum, egg tarts, and noodle dishes.

LOCAL’S TIP: For awesome burgers in a rock and roll environment, try Kuma’s Corner in Avondale. Their burgers are named after bands like Metallica, Slayer, Iron Maiden, and more. Expect it to be very busy, because locals love this place.

Burger at Kuma's Corner.
Burger at Kuma’s Corner.

2 pm: Explore a Neighborhood

To fully immerse yourself in the local culture, venture into vibrant neighborhoods like Pilsen, Lakeview, or Wicker Park.

Each neighborhood has its own distinct charm and personality, offering trendy shops, art galleries, and a diverse culinary scene.

I’ve got a complete guide to the coolest neighborhoods in Chicago. Here are a few worth checking out, away from the tourist areas:

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 tourists is the National Museum of Mexican Art, which features a diverse collection of Mexican art and artifacts.

pilsen Chicago

Andersonville: Here’s a charming neighborhood nestled in the heart of Chicago with a strong Swedish influence.

Walk the quaint streets lined with charming shops, cafes, and bakeries. For a deeper understanding of the neighborhood’s history, a visit to the Swedish American Museum is a must.

Lincoln Park: Visitors should definitely spend some time in Lincoln Park, a lively neighborhood renowned for its parks, as well as some great restaurants, shops, and walking trails along the lake.

The neighborhood is also home to the Lincoln Park Zoo and Oz Park, a parklet with statues of the characters from the Wizard of Oz.

Chinatown: Immerse yourself in the Chicago’s Chinatown. Tourists can wander through the streets, visit the unique shops and markets, and savor authentic Chinese cuisine.

Don’t miss the opportunity to explore the beautiful Chinatown Square and its traditional Chinese architecture. 

chinatown picture

Wicker Park: A trendy and eclectic neighborhood known for its arts and music scene and nightlife, Wicker Park is a great place to visit right on the Blue Line train.

Visit numerous art galleries, trendy shops, chic restaurants, and classic Chicago stores like Reckless Records.

Roscoe Village: Roscoe Village is not touristy at all. It’s a welcoming and family-friendly neighborhood with tree-lined streets, picturesque parks, and a plethora of boutique shops, from handmade crafts to trendy fashion.

Every July, the Roscoe Village Burger Fest showcases the neighborhood’s food culture, featuring burgers from local restaurants.

5 pm: Magnificent Mile Shopping and Dining

For a truly memorable shopping experience, head to the renowned Magnificent Mile. This upscale shopping district boasts an array of boutiques, department stores, and luxury brands that cater to every style and taste.

Take your time to explore the mile-long stretch of Michigan Avenue, stopping in to whichever gift shops and clothing stores look appealing.

Most Magnificent Mile stores are open until 7 or 8 pm, and you can grab dinner while you’re in the area.

Stop also at Tribune Tower, a historic building with pieces of other historic buildings embedded in it, like the Taj Mahal, the Great Wall of China, and the Berlin Wall.

8 pm: Catch an Improv Show

Chicago is known for its improvisational comedy scene. Second City is the most popular spot for Chicago improv.

That’s the famous club where dozens of famous actors and Saturday Night Live alumni got their start, including Tina Fey, Bill Murray, Stephen Colbert, Amy Poehler, and Steve Carrell.

second city improv

But smaller clubs like IO and the Annoyance Theatre also put on great shows, usually far cheaper than at Second City. And the quality of the shows at the smaller clubs is really good too.

Other Options for 2 Days in Chicago

There’s obviously so much more to do in Chicago that I haven’t covered in this 2-day itinerary! Here are a few other options that you may want to swap into your own schedule in place of something else.

Navy Pier: I find Navy Pier too touristy and not all that exciting, but your mileage may vary. Navy Pier offers a range of activities for tourists.

Visitors can enjoy views of Lake Michigan, ride the Ferris wheel, explore the Chicago Children’s Museum, or catch a show at the IMAX theater. Kids and families will enjoy the Ferris wheel.

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, visitors can sunbathe, swim, or take a walk along the waterfront. Popular beaches include North Avenue Beach, Oak Street Beach, and Montrose Beach.

lakefront trail

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.

Gangsters and Ghosts Tour: Delve into Chicago’s rich history with a Gangsters and Ghosts Tour. This guided tour takes visitors through the city’s notorious past, exploring famous gangster sites and haunted locations.

Frank Lloyd Wright House: Located in the suburb of Oak Park, Illinois, the Wright House stands as a testament to the architectural genius of its namesake.

The home and studio offer visitors an immersive journey into the architect’s innovative design philosophy. Built in 1889, the house showcases Wright’s ability to create functional spaces that blend with their natural surroundings.

frank lloyd wright house

Remember to check for special deals or discounts on attractions, especially if you plan to visit multiple museums or landmarks. Many offer discounted rates or free admission on certain days of the week.

Chicago Hotel Tips

Chicago offers a range of accommodation options for every budget. Consider staying in affordable hotels located in the city center, such as those in the Loop or River North neighborhoods. These areas provide easy access to major attractions and public transportation.

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

Palmer House Hilton – A historic hotel in the Loop, Palmer House Hilton provides a unique blend of vintage charm and modern amenities. Besides well-appointed rooms, it hosts a spa, fitness center, and several dining options, including the famed Lockwood Restaurant.

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, opulent rooms, and high-end dining options. It’s a stone’s throw away from top-notch shopping destinations and the beautiful Oak Street Beach.

HI Chicago Hostel – The most affordable lodging in Downtown Chicago is the HI Chicago, a hostel with dorm beds and private rooms. It’s not luxurious, but it’s in a perfect location, and the wifi and breakfast are free. I stayed here a couple times before I moved to Chicago, and always had a good experience.

A few additional tips for visiting Chicago in 2 days:

What’s the best time of year to visit Chicago? June is probably the best month. Summers in Chicago are epic, with lots of street festivals, fairs, and events. But temperatures in July and August can get really hot (above 90 F.)

June tends to be a bit cooler, and many of the best festivals take place in that month. Any time from April to November is fine. Winters are ok, but much colder.

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. Somehow, the nickname stuck!

Is it safe to visit Chicago? Sure. The city has the same amount of crime you’d find in any major American city. There are some dangerous neighborhoods in Chicago, but they’re generally not places that tourists tend to go.

What are some good day trips from Chicago? See my full list of day trips and road trips from the Windy City, including short trips to places like Milwaukee and Indiana Dunes National Park, as well as longer drives to Mammoth Cave National Park and St. Louis, via classic Route 66.

Looking for more Chicago vibes? See my photo gallery: 100 Pictures of Chicago.

Do you have any other suggestions for activities to include on a two-day Chicago itinerary?

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