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May 2024

Downtown Chicago Loop: 17 Fun Things to Do

Source: Choose Chicago

17 Fun Things to Do Near the Downtown Chicago Loop

Named after the elevated train tracks that encircle the central business district, the Downtown Chicago Loop is a hub of cultural, architectural, and culinary wonders. Whether you're a local looking for new experiences or a visitor eager to explore, here are 17 must-do activities in this iconic neighborhood.

1. Millennium Park

Source: Pexels

Start your adventure in the heart of the Loop at Millennium Park, a 24.5-acre urban oasis that houses the world-famous Cloud Gate, affectionately known as "The Bean." Stroll through the lush gardens, admire public art installations, and if you're visiting during the summer, catch a free concert or movie at the Jay Pritzker Pavilion.  Be sure to check local event listings, since there's a variety of things happening on any given weekend.

2. Buildings and Bites Tour

Source: Chicago Food & City Tours

Chicago is world renowned for its architecture. After all, we did invent the skyscraper.  But it can be hard to navigate the urban maze of tall buildings at the city's core to properly appreciate all that skyline at ground level.  It's best to have a guide.  Enter Chicago Food and City Tour's newest offering, Buildings and Bites, a 2.5 hour stroll through the Loop's main architectural corridor, a trail of Chicago's greatest architectural hits. Get the inside history on how each of these wonder-buildings came to be. This tour takes you from the Monadnock all the way to Willis Tower.  The best part - it's the only architecture tour that stops for a tasty lunch at the end!

3. Art Institute of Chicago

Source: Go Chicago

Art lovers won't want to miss the renowned Art Institute of Chicago, home to an extensive collection of art from various periods and cultures. Marvel at masterpieces by artists like Van Gogh, Monet, Picasso, and Grant Wood's iconic "American Gothic."  Don't forget to dip down to the basement for our favorite spot, the Thorne Miniature Rooms - an amazing collection of 68 shoe-box size rooms decorated to accurately reflect a variety of settings from history across the globe.

4. Chicago Architecture River Cruise

chicago river boat cruise tour
Source: Chicago Architecture Foundation

Discover the city's rich architectural heritage aboard a relaxing river cruise. Knowledgeable guides will regale you with stories about Chicago's most famous buildings, including the Willis Tower (formerly known as the Sears Tower) and the John Hancock Center. This is only 80-minutes long, so it's a perfect outing to squeeze in between a range of other tourist activities.  Put this one on the Can't-Miss list!

5. Iconic Foods of Chicago Food Tour

Source: Chicago Food & City Tours

Most cities are known for a single food, an iconic dish that came into existence through a combo of history and happenstance.  Not Chicago.  Chicago has four.  That's right, we've got a veritable Mount Rushmore of invented eats.  Deep dish?  That was us.  You like The Bear?  Yeah, we invented Italian Beef too.  What about that crazy mix of cheese and caramel popcorn that makes for a sweet and salty perfect pairing?  Thank you, Garrett Popcorn.  Oh, am I missing one?  Don't ever forget the hot dog heard 'round the world.  Wow, that's a lot of food.  Wanna taste them all?  Chicago Food and City Tours has you covered with their Iconic Foods of Chicago Tour.  Eat the whole Mount Rushmore of Chicago foods in one outing, and then they even thrown in a bonus Chicago classic for dessert!

6. Skydeck Chicago

Source: Arhinet

For an adrenaline-pumping experience, head to the Skydeck in the Willis Tower. Step onto "The Ledge," a glass balcony extending from the 103rd floor, providing unmatched views of the cityscape and Lake Michigan.  And don't worry, even if you find the thought of stepping out into the sky a little stomach-churning, the views from the regular Skydeck are worth admission themselves. It's a great place to give yourself a full perspective on just how impressive and sprawling the Second City is.

7. Chicago Cultural Center

Source: Conde Nast Traveler

Admire the stunning architecture of the Chicago Cultural Center, a landmark building hosting free art exhibitions, concerts, and cultural events throughout the year.  Be sure to head up to the top floor to see the Tiffany Dome.  Restored to its original splendor in 2008, there's a plethora of intricate details to admire all around the room.

8. Grant Park

Source: Chicago Traveler

Escape the hustle and bustle of the city at Grant Park, known as Chicago's "front yard." Take a leisurely walk, have a picnic, and enjoy the scenic beauty surrounding Buckingham Fountain.  If you've got little ones, hop over to nearby Maggie Daly Park, one of the best "playgrounds" the city has to offer.

9. Chicago Riverwalk

Source: Choose Chicago

Explore the Chicago Riverwalk, a lively pedestrian path that stretches along the south bank of the Chicago River. Take in the picturesque views, dine at waterfront restaurants, and rent a kayak or paddleboard for a unique perspective of the city.  For best eats on the riverwalk, we recommend Beat Kitchen.  For drinks, Chicago Brewhouse is a solid offering.

10. Chicago Symphony Orchestra

chicago classical music
Source: Facebook

Immerse yourself in the world of classical music by attending a performance by the internationally acclaimed Chicago Symphony Orchestra at Symphony Center.  Named One of the Best Orchestras in the World, they deliver the goods each and every time.

11. Chicago Theatre District

chicago architecture foundation
Source: Chicago Architecture Center

Catch a Broadway-quality show at one of the historic theaters in the Loop, such as the Chicago Theatre or the Cadillac Palace Theatre.  Broadway in Chicago has you covered for showtimes, directions, parking and any other info you might need.  All the big touring Broadway shows come through, some for limited engagements and others for extended stays. Hamilton set up shop for three years, they loved Chicago so much!

12. Maggie Daley Park

Source: Chicago Architecture Center

Perfect for families, this playful park offers a host of activities including a rock-climbing wall, mini-golf, and a whimsical playground.  It's a great place to go between museum visits, walking tours, and before you get ready to go out for dinner.

13. Chicago Riverwalk Art Galleries

Source: Splash Mags

Explore the diverse array of art galleries along the Riverwalk, showcasing works by local artists and photographers.  One piece, The Radiance of Being, sheds light on the city's art deco architectural past.  And if the Riverwalk isn't enough art for ya, check out the scene in nearby River North, the neighborhood with the densest collection of art galleries in the U.S. outside of Manhattan.

14. Dine at Revival Food Hall

Source: Open House Chicago

Satisfy your taste buds at Revival Food Hall, a modern food court offering an array of delectable dishes from some of Chicago's best chefs and eateries.  In a city famous for its food, food halls have exploded in popularity over the last decade.  Revival is absolutely one of the best in the city, with a diverse enough host of offerings to satisfy almost any hankering.

15. Chicago Pedway Tour

Source: Curbed Chicago

Discover the hidden underground walkway system, known as the Pedway, which connects several buildings in the Loop. It's a great way to navigate the city during inclement weather.  This systems is so on the D/L that most Chicagoans don't even realize we have a pedway.  Thanks to this cozy tunnel system, Inside Chicago is able to offer these tours year-round.

16. Chicago History Museum

Source: Go Chicago

Although not located directly in the Loop, this captivating museum is just a short ride away, offering fascinating insights into the city's history and culture.  A visit here is a great way to understand how Chicago came to be the incredible city it is today.  Plus, there's a giant toy Chicago-style hotdog there, so you can pretend to hop in as one of the special toppings like you've always dreamed of doing.  And if that culinary exercise makes you hungry, just head back downtown for another Chicago food tour.

17. Chicago River Kayak Tour

chicago kayak tours
Photo Source: Wateriders

Experience the city from a unique perspective by embarking on a guided kayak tour along the Chicago River. Paddle through the iconic skyline while learning about the city's architecture and history.

The Downtown Chicago Loop is a treasure trove of activities and attractions, catering to every interest and taste. Whether you're into art, architecture, culture, or simply want to soak in the vibrant atmosphere of the Windy City, these 15 activities are bound to create lasting memories of your visit to this iconic neighborhood.

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