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The Very Best Of Chicago In Two Days

Chicago is one of the most exciting cities in the U.S. and rightfully so! It has a its fascinating past, splendid architecture, top-notch museums, and expansive green spaces. This two-day itinerary will guide you to the very best things to do in Chicago to maximize your time!

Jun 2, 202313 min read

Anecia Ascalon
Anecia Ascalon
Team Building Expert

Chicago is one of the most exciting cities in the U.S. and rightfully so! It has a fascinating past, splendid architecture, top-notch museums and attractions, and expansive green spaces. But how to narrow down what to see if you only have a few days?

This two-day itinerary will guide you to the very best things to do in Chicago to maximize your time!

Day 1 Morning

Tour the Loop and Millennium Park

the Chicago Theater

After a quick breakfast at or near your hotel, start your introduction to Chicago by taking a walking tour offered by Free Tours by Foot. The Loop and Millennium Park Tour that covers part of Downtown Chicago, will give you an overview of Chicago’s architecture, history, public art displays, parks, and more. You’ll even stop at the start of the legendary “Route 66”! The tour starts at 10 am and lasts two hours.

Explore More of Millennium Park

Millennium Park

The Loop tour ends in Millennium Park, so take time to see more of this wonderful park by yourself. Millennium Park, located within the much larger Grant Park, is a much beloved outdoor haven for Chicagoans. There are captivating public artworks, innovative playgrounds, recreational areas, and lots of green space!

Head to The Bean (aka Cloud Gate) for the requisite selfie for Instagram! Check out the tall rectangular Crown Fountain and its unique digital video projections. In the warmer months, the fountain spews water!

Stroll through the serene Lurie Garden. If you are in Chicago with children, go to the adjacent Maggie Daley Park, which has a large rock climbing wall and a huge playground organized by age groups. In the summer the skating ribbon attracts rollerbladers and in the winter, it is transformed into a skating rink!

Lunch at Giordano's

deep dish pizza

When you are ready for some lunch, dig into one of Chicago’s most famous foods, deep-dish pizza. One of the top places to try this phenomenon is at Giordano's, one of the first family names in deep dish pizza in Chicago. They have a location at 130 E Randolph Street near Millennium Park. It’s just a ten-minute walk to the next stop on this itinerary.

Day 1 Afternoon

a painting in the Art Institute of Chicago

Art Institute of Chicago

This highly esteemed museum is south of Millennium Park at 111 S. Michigan Avenue Its collection is magnificent and any art lover will want to spend the whole afternoon here. Those who are merely interested in being exposed to more art should set aside an hour or two. Fans of the movie “Ferris Bueller’s Day Off” will recognize it instantly!

With over 300,000 artworks, the museum celebrates creativity from around the world throughout history. Perhaps the museum's most significant holdings are its impressive collection of Impressionist and Post-Impressionist paintings. The collection is so large that it is the largest outside the Louvre Museum in Paris!

If you happened to find yourself in Chicago on a rainy day, take refuge in the beauty of this world-class museum!

Day 1 Evening

The below activities can be enjoyed in any order!

The Escape Game Chicago

people playing an escape room

Before or after dinner, head to the River North neighborhood in Downtown Chicago for some excitement at The Escape Game Chicago! Once you enter one of their five “locked” escape rooms, you‘ll have just 60 minutes to find a way out. And how exactly do you escape? You’ve got to use all your brainpower to unravel riddles, solve puzzles and decipher clues.

If you succeed in this mission, you will be rewarded with your freedom. But even if you don’t figure out the answers in time, you will have a blast trying https://theescapegame.com/blog/o! Each escape room has a unique and imaginative theme and is masterfully crafted to create a realistic environment that complements the theme.

In The Heist, stealthily move between a museum gallery and a rogue curator’s office to recover a priceless painting. In Mission: Mars, you have to scramble to repair your spaceship stuck on Mars before a solar flare crashes into you! In Prison Break, feel what it's like to be locked in a cramped 1950s jail cell as you figure out how to bust your way out! Whatever game you choose, you’ll have lots of ‘wow’ moments and a fantastic time!

The Escape Game is family-friendly so if you are in town with kids or teens, stop on by!

Dinner at Eataly

The Escape Game is one block from Michigan Avenue and its lively nightlife scene. There you’ll have 275 restaurants to choose from! One standout just off of Michigan Avenue is Eataly Chicago, where you’ll find yourself in an Italian wonderland! Eataly is spread over two floors with two restaurants, and small food shops with counters for more casual dining. Save room for gelato!

Drinks at Cindy's Rooftop

To extend your first night out, go for drinks at Cindy's Rooftop on South Michigan Avenue. There are two spaces to sip on artisanal cocktails, wine, and craft beers - an airy glass atrium and an outdoor terrace. The views are special! Admire the sparkling skyline, and a view of Millennium Park, and Lake Michigan. Visiting Chicago for a Girls' Weekend? Cindy's was made for you!

Day 2 Morning

360 Chicago

view from 360 Chicago

You’ll want to get up early and grab a quick breakfast for a visit to this unforgettable attraction!

360 Chicago is an observation deck located on the 94th floor of the John Hancock Center. It’s one of the two observation decks in Chicago, the other being Skydeck, on the 103rd floor of the Willis Tower.

At 360 Chicago, you can enjoy a 360-degree view of the Chicago skyline and Lake Michigan as well as Chicago landmarks such as Millennium Park, Navy Pier, and the Willis Tower. On a clear day, the visibility can extend up to 55 miles, allowing visitors to see as far as four neighboring states!

One of the highlights of 360 Chicago is a ride called TILT, which offers those brave enough to try it a unique perspective of the city. TILT is a moving platform that tilts visitors outward from the building at a 30-degree angle, giving them a thrilling view of the city below.

Magnificent Mile

magnificent mile sign

From 360 Chicago, walk south along the “Magnificent Mile”. This one-mile stretch of North Michigan Avenue from East Lake Shore Drive to the Chicago River is a place to experience Chicago’s bustling energy. Shopping is one of the main attractions along the Magnificent Mile. It is a shopper's paradise with a wide array of luxury boutiques and department stores.

Architecture enthusiasts will be captivated by the stunning buildings that line the Magnificent Mile. The area boasts a mix of architectural styles, from historical landmarks to modern skyscrapers. Some notable structures include the Wrigley Building, the Tribune Tower, and the iconic Chicago Water Tower, one of the few buildings that survived the Great Chicago Fire of 1871!

Walk all the way to the River to see the historic DuSable Bridge constructed in 1920. This pedestrian-friendly bridge is notable for its distinctive Beaux-Arts style design, with bronze sculptures and balustrades with decorative light fixtures. It’s a draw bridge, which isn't seen very often in large cities! It’s a marvelous walkable bridge in a city filled with skyscrapers.

Lunch: Chicago Hot Dogs

Chicago Hot Dog

Another famous Chicago food is a hot dog - served the Windy City way! A Chicago hot dog starts with an all-beef frank tucked into a poppy seed bun. Then comes the yellow mustard, pickled sport peppers, chopped white onions, sweet pickle relish, tomato slices, and a dash of celery salt. Last but not least, a dill pickle spear is placed on the top.

There are plenty of places to grab a Chicago hot dog. Here are two that are located somewhat near the attractions you’ll be on Day 2. The most famous place in the area where you will be is Portillo’s, though it's a few blocks farther out from the next destination. Instead, opt for Devil Dawgs, which is more convenient and also delicious!

Day 2 Afternoon

Museum Campus

The Field Museum

Museum Campus is a large, lovely green space that sits along Lake Michigan. The main draw here is the exceptional museums and institutions: the Field Museum of Natural History, the Shedd Aquarium, and the Adler Planetarium.

(Take note that if you are in Chicago on a hot day and outdoor sightseeing is a bit too uncomfortable, Museum Campus can keep you occupied for hours and hours!)

The first museum you will encounter on the campus is the Field Museum of Natural History. The Field, founded in 1893, is widely regarded as one of the most famous natural history museums in the world. One of the monumental collections in the Field is its dinosaur fossil collection which includes SUE, the largest and most complete T.rex ever discovered! Other outstanding permanent exhibitions are “Evolving Planet” which covers the evolution of life on Earth over 4 billion years and “Inside Ancient Egypt” artifacts from everyday life and of course, mummies!

Next up is the Shedd Aquarium, a sensational attraction where visitors are able to see more than 32,000 aquatic animals including dolphins, beluga whales, penguins, sea turtles, sea otters, and so many other beautiful sea creatures! The Coral Reef exhibit is contained within a glass tank that you can walk around for a 360-degree view of life in this habitat. The Wild Reef exhibit puts you face to face with several different types of sharks. You can participate in one of the Shedd Aquarium's animal encounters to get up close and personal with penguins, and even feed some of the animals!

Last in the trio is the Adler Planetarium, the first planetarium in the country. It’s not as large as the Shedd Aquarium or the Field Museum, but if the cosmos has always fascinated you, then the Adler should hit the spot. There are three theaters to see space shows. The Grainger Sky Theater was designed as a virtual observatory. Exhibits are informative and intriguing. There are also lectures and hands-on educational programs.

At this point, you may be worn out and ready to crash at your hotel! Take some time to rest up, grab a light dinner, then get ready for a sunset on the Chicago River!

Day 2 Evening

Nighttime Cruise in the Chicago River

night cruise on the Chicago river

One of the activities not to be missed when in Chicago is taking a nighttime cruise on the Chicago River. By this point in your trip you have seen some of Chicago’s remarkable architecture -- but it’s a whole different ball game when experienced at night. Watching the dazzling skyline reflect on the river is a special way to experience Chicago’s iconic buildings. Wendella Boat Tours offers both 45-minute and 90-minute architecture cruises that depart as late as 10 pm.

An alternative to a river cruise is to stroll along Chicago’s treasure, Riverwalk. This picturesque 1.25-mile-long path along the Chicago River is dotted with public art installations, restaurants, and bars. If you are traveling as a couple and looking for something romantic to do in Chicago, a nighttime cruise or strolling Riverwalk can do the trick!

Navy Pier

Navy Pier at night

A popular attraction in Chicago for more than a century! It’s an easy-going place for those seeking fun and a lively night out. You can visit the Boardwalk and enjoy amusement rides at Pier Park like the Centennial Wheel that offers amazing views of the city and Lake Michigan from 200 feet up!

Then do some light shopping and grab food at one of several restaurants. Stop for a drink at the Offshore Rooftop & Bar, the country’s largest rooftop bar! If you are here in the summer, you are in for a treat. On Wednesday and Saturday nights, there is a fireworks display at Navy Pier.

See our article, 25 Things To Do At Night In Chicago, for more ideas.

If you are in Chicago for more than two days or want suggestions for alternative activities to those above, check out our comprehensive guide to Chicago!

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