Perfect Chicago 2 Day Itinerary

Chicago, on Lake Michigan in Illinois, is among the largest cities in the U.S. Famed for its bold architecture, it has a skyline punctuated by skyscrapers. Two days in the city offers a chance to try some of the most iconic foods, unique history, speakeasies, and more.

I’ve officially been to Chicago in every season but fall and have to say – spring might just be my favorite. I absolutely loved this trip to Chicago and highly recommend taking the time to spend a few days here. You can see most things in just 2 days, but could definitely spend longer.

As someone who’s been several times, this is definitely a perfected itinerary that gives you a bit of everything. There’s tons of fun and cheap things to do in Chicago and I may have found the perfect way how to spend two days in Chicago.

Table of Contents

Where to Stay in Chicago

If you want to book a hotel in Chicago that won’t cost $1000 for the weekend (literally), book far in advance! We looked a month out and had no options. We ended up staying at a shared Airbnb that had an on-suite bathroom just a 10-minute drive from downtown. Even that was $100 a night! Below are three hotel recommendations from more affordable to luxury.

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.

The Robey

Perched high above the big intersection of Damen, Milwaukee and North Avenues in an Art Deco masterpiece formerly known as the Northwest Tower—stretching 203-feet tall and the only skyscraper for miles—The Robey captures the storied spirit of Chicago: a bustling, ever-changing, big-shouldered town.

The Langham

Just 2 blocks away from the famed shopping, dining and entertainment on Michigan Avenue’s 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.

Tips for Visiting Chicago

  1. Visit the Museums: Chicago is home to some of the best museums in the world. Don’t miss the Art Institute of Chicago, Museum of Science and Industry, Field Museum, and Shedd Aquarium. Consider purchasing a CityPASS or Go Chicago Card for discounted admission to multiple attractions.
  2. Sample the Food: Chicago is famous for its food scene, from deep-dish pizza and Chicago-style hot dogs to gourmet restaurants and ethnic eateries. I’ll share some top spots in this itinerary!
  3. Public Transportation: Chicago has an extensive public transportation system, including buses and the ‘L’ (elevated train). Purchase a Ventra card for easy access to public transit, or use rideshare services like Uber and Lyft for convenience.
  4. Pack for the Weather: Chicago experiences all four seasons, so pack accordingly. Summers can be hot and humid, while winters can be cold and snowy. Spring and fall offer milder temperatures but can be unpredictable, so layers are key. It’s also called the windy city for a reason, prepare for wind in every season!
  5. Safety: Like any major city, it’s essential to stay aware of your surroundings and take precautions to ensure your safety. Stick to well-lit areas, avoid walking alone at night in unfamiliar neighborhoods, and keep your belongings secure.
  6. Plan Ahead: Chicago has so much to offer, so it’s a good idea to plan your itinerary in advance to make the most of your time. Check out event calendars, restaurant reviews, and attraction hours to avoid disappointment and make the most of your visit.
  7. Consider getting the Go City Pass: If you’re doing several of the activities recommended in this itinerary, consider getting the pass to save money!

Day 1

Okay so this day is going to seem really packed! But here’s the thing – we were running out of things to do on this day because everything was really close together and is more about seeing the sites than doing an activity. We had hours of free time between activities which meant day drinking and relaxing (perfectly fine with me!).

Hero Coffee

Hero Coffee is a local coffee chain found throughout Chicago. We found this cute spot right downtown in a cool alley way and it was a relaxing first stop for a coffee and chocolate croissant.

Chicago Theater

Armed with iced coffee, we walked a few blocks to the Chicago Theater. This is a must see and if you have time, definitely go see a performance. We checked online but nothing was happening while we were there.

The Chicago Theater is famous for many different reasons. First, it has a beautiful facade and has hosted many famous musicians and performers. It was also the venue for some of the most extravagant parties Al Capone held during his days in Chicago. This was along our walk, so it was an easy stop. We also went by here later on our ghost tour.

If you buy the Go City Pass, a tour of the Chicago Theater is part of the attractions covered! Consider spending an evening at a show at the Chicago Theater as well.

Millennium park

Millennium Park is large and beautiful. We loved walking around and seeing all the beautiful views of the city from inside the park. “The Bean” is the most famous piece of art in the park and worth the stop! At 10 am it was already extremely packed but we did get to snap a good selfie and walk through.

Make sure you walk through the bean for some really cool reflections and views. The buildings reflecting off of it were stunning as well.

Here are some of the top sights in Millennium Park:

  1. Cloud Gate (The Bean): Perhaps the most iconic feature of Millennium Park, Cloud Gate is a massive, reflective sculpture created by artist Anish Kapoor. Its mirrored surface reflects the Chicago skyline and the park’s visitors, making it a favorite spot for photos and selfies.
  2. Jay Pritzker Pavilion: Designed by architect Frank Gehry, the Jay Pritzker Pavilion is an outdoor concert venue with a distinctive, undulating roof made of stainless steel. It hosts a variety of events, including concerts, festivals, and outdoor movie screenings, especially during the summer months.
  3. Lurie Garden: This beautiful, four-season garden is a peaceful oasis within Millennium Park. Designed by landscape architect Piet Oudolf, it features a variety of native plants, perennials, and trees, as well as walking paths and seating areas.
  4. Crown Fountain: Designed by Spanish artist Jaume Plensa, the Crown Fountain consists of two 50-foot towers facing each other across a shallow reflecting pool. The towers display digital images of Chicago residents’ faces, which periodically spout water into the pool, creating a playful and interactive experience for visitors.
  5. BP Pedestrian Bridge: This elegant pedestrian bridge, designed by architect Frank Gehry, connects Millennium Park to Maggie Daley Park and the lakefront. Its winding form and curving lines offer beautiful views of the city skyline and the surrounding landscape.
  6. Wrigley Square and Millennium Monument: Located at the northwest corner of Millennium Park, Wrigley Square features a beautifully landscaped lawn and gardens, as well as the Millennium Monument, a nearly 40-foot tall Doric-style limestone column.
  7. Nichols Bridgeway: This pedestrian bridge connects Millennium Park to the Art Institute of Chicago’s Modern Wing. It offers panoramic views of the park and skyline as you ascend to the museum.
  8. McDonald’s Cycle Center: Located underneath Millennium Park, this state-of-the-art facility provides secure bike parking, rentals, repairs, showers, and other amenities for cyclists exploring the city.
  9. Art Installations and Sculptures: In addition to its permanent features, Millennium Park often hosts temporary art installations and sculptures by local and international artists. Keep an eye out for rotating exhibits and installations during your visit.

Navy pier

From Millennium Park we walked to Navy Pier. In my mind, this stop is a must while in Chicago because it gives the best view of the city and some fun. It’s home to the Children’s Museum, boat tours, lots of restaurants, shops, and rides.

Fun fact – did you know 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 as Americans do… 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. The original Ferris Wheel was not at Navy Pier but it is cool to ride one where the Ferris Wheel was invented.

Hours: Sunday – Thursday, 11:00 am – 8:00 pm; Friday – Saturday, 11:00 am – 9:00 pm

Pro-tip: Bars on Navy Pier offer alcoholic drinks to go. You can actually drink anywhere along the pier freely. Yes please! We took advantage of this after our Ferris wheel ride relaxing as we were waiting for lunch.

Here are some top things to do at Navy Pier, beyond the Ferris Wheel (ps several are on the Go City Pass, including the Ferris Wheel):

  1. Chicago Children’s Museum: Explore the Chicago Children’s Museum, located on Navy Pier, which offers interactive exhibits and hands-on activities for kids of all ages. From water play to construction zones, there’s plenty to keep children entertained and engaged.
  2. Chicago Shakespeare Theater: Catch a show at the Chicago Shakespeare Theater, which presents a wide range of classic and contemporary productions in its state-of-the-art theater space overlooking Lake Michigan.
  3. Boat Tours and Cruises: Navy Pier is a departure point for various boat tours and cruises on Lake Michigan and the Chicago River. Choose from architectural tours, sightseeing cruises, fireworks cruises, and more to explore Chicago’s skyline and waterways.
  4. IMAX Theater: Watch a movie on the big screen at the Navy Pier IMAX Theater, which offers immersive experiences with its giant screen and state-of-the-art sound system. Check the schedule for current showings and special presentations.
  5. Pier Park: Enjoy outdoor fun at Pier Park, which features attractions such as a carousel, wave swinger, mini-golf course, and remote-controlled boats. It’s a great place for families and thrill-seekers alike to enjoy rides and games.
  6. Shopping: Browse the shops and boutiques at Navy Pier, where you can find souvenirs, gifts, apparel, jewelry, and more. Pick up a memento to remember your visit to Chicago.
  7. Live Entertainment: 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.

Deep dish

Deep dish pizza is a famous dish invented in Chicago. It’s more rich than your typical pizza and fills you up quick. If you choose to go somewhere downtown, even for lunch, you will most likely end up with a wait. We put our name on the list at Giordano’s Navy Pier location and the wait was 1 hour. There are lots of bars though so we grabbed a drink while we waited.

Chicago style deep dish has the cheese, and things we typically think as toppings, underneath a layer of sauce. It is cooked in an extra deep pan (surprising given it’s name right?!) and is very filling. With three of us, we ordered a medium plus an appetizer and ended up with a piece left – more filling than your typical pizza.

Chicago riverwalk

After lunch we were full and needed to walk off the giant pizza we ate! It was time to walk the riverwalk that is just stunning. Chicago is built along a river, and the views are just gorgeous! Walk along the water and across bridges for great views (there are many). City Winery has a great spot on the water with tables and delicious wine to take in the views.

We again took some time to relax along the waterfront and enjoy the epic views (are you seeing a pattern?! Tons of great views in Chicago).

Gangsters and Ghosts Tour

I always like to fit in a little history while in a city and the gangsters and ghosts tour was the perfect way to do it. We spent about 2 hours walking around and checking out the spots that are most famous for, well, gangsters and ghosts!

There’s also a Mobsters and Haunted Mysteries tour in the Go City Pass.

During the tour, we got the chance to see some of the most famous buildings in Chicago as well as hear the history. We walked from the riverwalk to the Chicago theater to more. Chicago has a history, especially with prohibition and the industrial revolution so I highly recommend going on this tour if you want to hear some of the secret and interesting history of the city.


The other food Chicago is famous for is the Chicago dog. The hot dog is topped with yellow mustard, chopped white onions, bright green sweet pickle relish, a dill pickle spear, tomato slices or wedges, pickled sport peppers and a dash of celery salt. One of the top spots, Portillo’s, ended up being right near a speakeasy that was recommended to us on our tour. We knew we had to check it out!

Portillo’s has many different counters and you can order hot dogs, brats, and more at the different counters. It can get very crowded during the day, but has ample seating and space for people to relax. We were there later in the evening around 8 and so it was not crowded at all.

It was so delicious and their French fries definitely hit the spot too.

The Drifter – An Original 1920s Speakeasy

We ended up choosing this speak easy because it was close to where we were, but also, came highly recommended. It’s located in the bottom of the Green Door Tavern. You have to go through a bookcase next to the bathrooms in the basement. It was a working speakeasy all the way through the 1920s prohibition and they have kept the vintage feel of the bar.

All the drinks are listed on tarot cards, and my boyfriend couldn’t stop ordering the Miz McFlury because it was so good (okay, fine, I ended up ordering it too because YUM!). They also have live entertainment nightly and if you want to see what a speakeasy was like, this is the spot to do it.

Godfrey Hotel Rooftop Bar

We walked just two blocks over to a rooftop bar to get another great view (surprise!). The Godfrey was the perfect spot to take in a view, even though it was cloudy, and grab a final drink before Ubering home.

Pro-tip: Many people were dressed up at this spot but I was in ripped jeans and tennis shoes. The bouncer didn’t say anything and we were able to order drinks no problem. They had fire pits and quiet spaces outside which had a very different feel than the inside space which felt a bit like a club. It was a great view!

Day 2

After a full day, take it easy on your second day and start a little later. We stopped at a random diner during our bike ride along the way to our first stop.

Bike along the Lake

We had a Divvy Bike station right next to our AirBnB which made hopping on a bike super easy. Divvy Bike is Chicago’s bike share program. You can rent one of their bikes from any station around the city (there are tons!) and ride from spot to spot. A single ride is $2 or rent for the day for $15 so because we were planning to ride several times, we chose to rent for the whole day giving us freedom to bike everywhere we wanted to go.

I always try to fit in some sort of physical activity on a trip. Biking along the lake was not only gorgeous, but also gave us a chance to see the city from a different side. We stopped at 31st Street Beach for the view and continued on into the city to the Chicago Institute of Art.

If it wasn’t for the rain that weekend, we may have gone kayaking in Chicago on the river (it looks like so much fun!). Definitely something worth checking out if you go.

Don’t want to do this alone? Book a bike tour instead!

Art Institute of Chicago

I love museums and was very impressed with this one! It’s one of the top rated museums in the world with almost every type of art you can think of. Their impressionist collection was huge and I loved seeing all the Monet paintings the most. The flow is a little confusing but you’ll easily get around using a map.

We bought our tickets online which saved us a bunch of time. We were also carrying our bags around this day, and baggage check was just $1 a bag, so we decided to leave our bags there for the rest of the day. It was really easy and convenient.

Hours: 11:00 am-5:00 pm

Cost: Adults $32, Seniors, Teens, and Students $26, Children under 13 free

Bike the Magnificent Mile

The Magnificent Mile is Chicago’s premier commercial district, famous for the shops and important buildings along Michigan Avenue, which runs through downtown Chicago.

The vibrant, bustling area is home to upscale shops and more. We were headed to a spot down the Magnificent Mile, and with our full-day bike rental, it made sense just to bike! It was fun to ride the bike lane through downtown, though, and get a closer look at all the shops as we rode past.

Cocktails at The Signature Lounge 

There are a few options of observation decks in Chicago like the glass floor at at the Chicago SkyDeck. I actually ended up seeing the Signature Room at Willis Tower on someone’s Instagram story and knew I had to visit! It’s free to enter this beautiful bar, but the price of a cocktail is the same as admission onto an observation deck.

The Signature Lounge is just two floors down (96th floor) from the observation deck above. We loved sitting and sipping our drinks though overlooking the entire city of Chicago though instead of wading through tourists. It was beautiful and the fact that a drink was included was worth it.

There’s also a restaurant located on the same floor of the building, but you will need a reservation to go!

Pro-tip: The Signature Lounge gets really crowded as the day goes on. We went around 2:30 and there was no wait. However, when we left at 4:00, there were at least 20 people waiting. Go early if you can.

Goose Island Brewery

It wouldn’t be a trip with my boyfriend if we didn’t stop at a brewery! We headed to Goose Island, which was perfect because it was on the way to the airport, and it was fun to check out a brewery we knew but also get to taste their special brewery-only beers. It was a Sunday afternoon and very chill with few people inside drinking, so it was a relaxing stop for sure. We each were able to create our own flight and try a bunch of fun beers.

Fatso’s Last Stand

This was another hot dog spot (yes I do recommend eating hot dogs two days in a row – so what!) that came highly recommended and was pretty close to Goose Island and again, on the way out of town. The hot dogs were delicious and the mac and cheese was sooo creamy. Fatso’s is known for the cheese they add to their traditional Chicago dog and it was pretty delicious. It was a perfect last stop before heading to the airport.

Other Suggestions for Visiting Chicago

  1. Chicago River: 1.5-Hour Guided Architecture Cruise: Experience Chicago’s legendary architecture from the best seat in the house: the river. Enjoy a comprehensive tour with a live fun guide as you navigate through the heart of the city covering all 3 branches of the Chicago River.
  2. 1.5-Hour Romantic Sunset Cruise: Watch the sun slowly set behind the city from the tranquil waters of Lake Michigan on this serene and romantic cruise. Toast the end of the day with a glass of wine, ice-cold beer or hand-crafted cocktail.
  3. Explore the largest science center in the Western hemisphere with this ticket to the Museum of Science and Industry in Chicago. Bring science, technology, and engineering to life through exhibits.
  4. Explore the Neighborhoods: Chicago is a city of diverse neighborhoods, each with its own character and attractions. Don’t limit yourself to downtown; explore areas like Wicker Park, Lincoln Park, and Pilsen to get a taste of local culture and cuisine.
Discover the perfect itinerary for spending two days in Chicago. Explore the city's stunning architecture, unique history, and vibrant food scene.
Discover the perfect itinerary for spending two days in Chicago. Explore the city’s stunning architecture, unique history, and vibrant food scene.

We loved Chicago, and I know you will, too! I hope this guide was able to help you as you plan how to spend two days in Chicago.


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