I fell in love with Chicago many years ago. Back in the tenth grade, I traveled on a high school band trip to Chicago with a busload of fellow band geeks. Years later, I'd return a few times as an adult and fell in love with the city all over again.
Here's how to spend 2 days in Chicago, enjoying a good mix of must-see tourist hot spots and lesser visited neighborhoods that I adore. Chicago often gets compared to New York City or Toronto. It has an entirely unique vibe, including a handful of totally unique attractions.
Chicago has been voted as the "Best Big City in the US" by Conde Nast for many years in a row, and it's easy to see why it's continuously awarded this accolade. It's a world class destination for its music scene, architecture and museums.
The Windy City is also a great place to live if you're thinking about moving to a city in the USA.
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Why I Love Chicago
There are so many reasons to visit Chicago. I've been a handful of times now and keep returning. I'm sure you'll fall in love, too!
- Amazing Architecture: Chicago is well-known for its architecture, which you can discover on foot or by boat cruise. There's even an entire museum devoted to the city's architecture.
- Walkability: Chicago has many diverse neighborhoods and they're all super walkable. And when you need to get from one to the next, consider taking the really convenient public transportation system.
- Incredible Food Scene: Chicago has an awesome food scene, including independently owned coffee shops. Famous for its Chicago-style deep dish pizza, you'll have to try some when you're there.
2 Days in Chicago Itinerary: Where to Stay
With a limited amount of time in Chicago, it's vital to plan your weekend in advance. Once you get your flights in order, it's time to choose a hotel.
I'd consider Chicago to be an expensive city, so plan your budget wisely. If you'd like to splurge on activities and experiences, you might want to save money in order places, like booking a cheap hotel in Chicago.
On the other hand, for a romantic or luxurious stay, opt for a more expensive hotel while saving money in other places. For instance, try some free activities like admiring architecture, street art, and public gardens. Feast on cheap, yet delicious, street food.
2 Days in Chicago Itinerary: Day 1
For our first day in Chicago, we'll stick mainly to the downtown core. We're going to see Chicago's famous architecture, monuments, public spaces, parks and gardens on the waterfront.
We'll finish off the day with a trip to 360 Chicago to view the city from high up above. Try to aim your visit around sunset to enjoy panoramic scenery of the sun going down.
Cloud Gate ("The Bean")
One of the most popular and recognizable monuments in Chicago is Cloud Gate, better known as "The Bean". It's located in Millennium Park in downtown Chicago.
I suggest that you start your day here. It's a good idea to arrive early if you'd like to capture a photo without the crowds. In the photo above, I got to The Bean around 8:00am and there weren't any tourists around.
Cloud Gate was created by British artist Anish Kapoor, and it is his first work of public art in the USA. Its stainless steel surface perfectly reflects the Chicago city skyline and clouds.
It's possible to walk beneath The Bean and you can capture some interesting reflections of yourself, too. The sculpture measures 66 feet long by 33 feet high, and it's the largest work of public art of its kind in the world.
The Art Institute of Chicago
The Art Institute of Chicago is one of the best art museums and attractions in the USA. If there's one museum you visit in Chicago, this is the one.
There are thousands of works of art here spanning across the ages. While I think you should explore the entire museum, the official website has a great guide to visiting in an hour, if you have a limited amount of time.
Some of the most famous pieces of art here include Self-Portrait by Vincent van Gogh, Sky Above Clouds by Georgia O'Keeffe, American Gothic by Grant Wood, The Old Guitarist by Pablo Picasso, and the Hartwell Memorial Window by Agnes F. Northrop and made by Tiffany Studios.
Not as much of an art fan? Some great alternatives to The Art Institute of Chicago are the Field Museum or Adler Planetarium, located not too far away.
Grant Park
While Millennium Park and The Art Institute of Chicago are technically part of Grant Park, I urge you to continue exploring this 319 acre public park in Chicago. Located in Chicago's Loop, it's similar to visiting Central Park in New York City.
Grant Park is close to the waterfront with walking paths and bike paths along Lake Michigan. There's also a beautiful rose garden that I've been fortunate enough to see in bloom twice now. Both of my most recent visits to Chicago have happened to be in June.
Don't miss the impressive Clarence Buckingham Memorial Fountain, built in 1927 to serve as a focal point of the park. It's quite spectacular to witness this massive fountain with the city skyscrapers as a backdrop.
Architectural Boat Tour
One of the best things to do in Chicago is an architecture boat tour aboard First Lady. If you have 2 days in Chicago (or even only 1 day in Chicago), this is the ultimate tour to take in the city.
It's such a great way to see the city, learn about its history, and see the architectural marvels that line the waterways. You won't see views like these anywhere else in the city. You'll see landmarks like the Wrigley Building, Marina City, and Willis Tower.
First Lady cruises put architecture first and they are the only cruise that partners with the Chicago Architecture Center. It's been rated as the #1 boat tour in Chicago by Tripadvisor. The tours are about 90 minutes long, so it'll only take up a small portion of your afternoon.
Chicago Riverwalk
After you see the river by boat, why not take a stroll down the famed Chicago Riverwalk? This is an expansive walkway that follows the river with many restaurants, cafes, shops and place for photo opportunities.
Even if you simply walk up and down the Riverwalk, it's a must when you're in the city. If you want to get up close and personal with some of the attractions on the Chicago Riverwalk, check out the McCormick Bridgehouse & Chicago River Museum.
Magnificent Mile
The Magnificent Mile, also known as Michigan Ave., is a destination for shopping and entertainment in downtown Chicago. This is where you'll find the luxury boutiques, world-class dining, live shows and more.
In total, there are over 460 retailers and three shopping malls. Even if shopping isn't really your thing, take a stroll on the Magnificent Mile to spot some unique architecture and timely events.
360 Chicago
360 Chicago, otherwise known as the John Hancock Observatory, offers some of the most amazing 360 degree panoramic views of Chicago. Travel by elevator up to 1030 feet above the city for unparalleled, stunning scenery.
Want to make your visit even more thrilling? Try the TILT ride! Stand in a special glass area and hold onto the handlebars. The tilting glass ledge allows you to lean forward, directly over the city down below.
I suggest going at sunset, though visiting anytime during the day or night is a good idea. If you have time, you can visit once during the day and once at night for completely unique experiences.
Navy Pier
Navy Pier is fun for the whole family! It offers a massive indoor and outdoor complex with dining options, activities, attractions, shopping and more. It's also simply a great place to soak up the views and go people watching.
The Centennial Wheel is a romantic way to get panoramic views of Lake Michigan and the Chicago skyline. There's also a fun fair and arcade to indulge your inner child. If you visit at night, there are free fireworks shows on Wednesdays and Saturdays between May 24th and August 30th.
Did you know that you can take a seasonal water taxi from Navy Pier to other locations along the river and lake? There are stops at Union Station, Michigan Ave, Navy Pier, and Shedd Aquarium/Museum Campus. There's nothing like sailing towards Navy Pier for the best Chicago skyline scenery.
2 Days in Chicago Itinerary: Day 2
For our second day in Chicago, it's time to visit some of the city's vibrant neighborhoods. Chicago is a city made up of many diverse neighborhoods.
It's easy to depart the city center to visit Pilsen, Wicker Park and more. Use Chicago's "L" (short for elevated), the fourth-largest rapid transit system in the USA. Trains serve more than 140 stations across the city, making it really easy to get around town.
Of course, there's always Uber or taxis as an option, too!
Pilsen Neighborhood
One of my favorite neighborhoods in Chicago is Pilsen. This area of Chicago is rich in Latino culture, and it's the place to be for music, art and culture. Even with only 2 days in Chicago, it's worth the trip outside of the downtown core.
There are colorful and vibrant murals, mostly on 18th Street and 16th Street, though they're everywhere if you're on the lookout. In fact, 18th Street in Chicago has been named as one of the coolest streets in the world by Time Out.
I highly recommend going for lunch at Penelopes Vegan Taqueria Pilsen and enjoying a coffee at Cafe Jumping Bean. Pilsen Community Books was another favorite stop of mine. It's Chicago's only employee-owned and operated independent bookstore.
National Museum of Mexican Art
The National Museum of Mexican Art features a vast collection of Mexican art and culture. Enjoy art from across the ages, from ancient to modern, and everything in between.
Founded by 1982, this museum represents the Mexican community. It's home to one of the country's largest Mexican art collections, including over 22,000 pieces.
The museum is always free to visit (though you can leave a donation if you'd like). There are a few different rooms to wander through, and some of the items on display may be part of limited exhibitions. There's always something new to see here, so it's worth returning multiple times.
Garfield Park Conservatory
Garfield Park Conservatory is a little off the beaten path, but I think it's worth the extra journey. For fans of botanical gardens and plants, you won't want to miss it. It is one of the largest botanical conservatories in the nation.
There are eight indoor display gardens featuring plants from all over the world. There are also more than 10 acres of outdoor gardens, including a water lily pond.
Especially in the wintertime, the climate remains tropical all year long, so it's a great escape from the harsh winter weather. I visited in June and it was lovely to be able to wander in the greenhouses and outdoors as well.
Wicker Park
Here's another great neighborhood to visit, even if you only have 2 days in Chicago. Wicker Park is an artsy and hip spot in Chicago to experience with unique restaurants, nightlife, live music venues, independently owned shops and more.
If you have the time, why not walk a section of The 606? A portion of this elevated trail goes through Wicker Park.
Wicker Park is also home to some fabulous street art. The photogenic Chicago mural, pictured above, is one for your Instagram for sure. There's also a massive mural of Robin Williams.
Some other places I adored in Wicker Park include Wormhole Coffee, Myopic Books, and No Bones Beach Club. Even the Barnes & Noble location in Wicker Park is an architectural beauty that's unlike any B&N I've ever seen!
Headquarters Beercade
Venturing back towards downtown Chicago, Headquarters Beercade is perfect for arcade and gaming lovers. Justin and I love frequenting arcades when we travel, and this one is brilliant!
They've got over 70 pinball machines and vintage arcade games that will keep you busy all evening. One of the best parts? They're all free to play!
You can also dine or enjoy a pint or two while you're here. HQ Beercade also puts on many fun events, so you'll have to check their schedule to see if anything aligns with your 2 days in Chicago.
48 Hours in Chicago: Stay Longer if You Can!
Sometimes all you get is a weekend in a place, and this action-packed 2 day itinerary makes for an amazing adventure. However, I suggest staying longer in Chicago if you can.
Definitely spend at least 2 days in Chicago if you can, if not longer. At least 3 to 5 days will allow you to visit many attractions and neighborhoods.
This is a great way to spend 48 hours in Chicago, especially if you're visiting for the first time. But, you could spend weeks and weeks in the city to uncover all of its gems. For this reason, it's a wonderful city to return to again and again.
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