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What to do in Downtown Chicago | What to do in The Loop

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A complete guide of what to do in downtown Chicago! The heart of downtown Chicago is called “The Loop” since the el (the train) makes a square loop around this part of the city. 

A complete guide of what to do in downtown Chicago - all the best things to do, restaurants, events, places to stay, and parks.

This is the business center of the city filled with skyscrapers and office buildings. This area has a more industrial feel and parts of this neighborhood can be somewhat empty on weekends and at night. That’s because most Chicagoan’s live outside the Loop. It doesn’t have the neighborhood feel that other areas have.

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What to do in Downtown Chicago

See Cloud Gate (The Bean)

This sculpture in the shape of a bean is one of Chicago’s most recognizable landmarks.

Grant Park

This large park is just beside Millennium Park and Maggie Daley Park. It is home to Buckingham Fountain and the location of events like Lollapalooza and the Taste of Chicago.

Millennium Park 

Located between Cloud Gate, the Art Institute, and Maggie Daley Park, Millennium Park’s centerpiece is the Jay Pritzker Pavilion. This stage is home to concert and film series in the summer.

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Maggie Daley Park

A large park with a series of playgrounds for children of different ages. Plus in the winter there is a skating ribbon for ice skating.

Architectural Boat Tour

The Chicago Architecture Foundation’s river cruise is one of the best things for tourists to do in Chicago. The tour takes you down the Chicago River and covers the history of Chicago and the evolution of the city’s architecture. It’s fun, informative, and there is a full bar onboard.

This tour is seasonal and is not offered in the winter.

Rent a Boat / Kayak the River

If you want to spend time on the river without doing a formal tour, there are companies that rent kayaks and small motor boats so you can paddle or cruise up the river.

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The Riverwalk is a 1.25 mile walking path on the south side of the Chicago River that takes you right through the heart of downtown. The Riverwalk is open from 6 am – 11 pm and in the warmer months there are restaurants open along the walkway.

Visit Willis Tower

The tower formerly known as the Sears Tower is still the tallest building in Chicago. At the top of the tower there is an observation deck plus The Ledge, a small observation deck with a glass floor.

Art Institute of Chicago

If you are going to visit one museum in Chicago, this should be the one. Considered to be one of the best museums in the world, the Art Institute of Chicago has an exceptional collection of Impressionist and Post Impressionist Art and hosts traveling exhibits.

The Chicago Theater

This theater in The Loop is the place to see concerts, comedy shows, and other touring shows. I love this theater because it isn’t too big and every seat feels like a good seat.

Buddy Guy’s Legends

A blues club with live music 7 nights a week. They also serve New Orleans inspired food. The club was opened in 1989 by blues musician Buddy Guy, and if you are lucky (like I was!) he might just hop up on stage and perform. You might want to buy tickets in advance.

Broadway in Chicago 

There are a handful of theaters in Chicago that are home to Broadway in Chicago plays and musicals. Some are Chicago based productions and others are touring shows.

Annual Events in Downtown Chicago

A Comprehensive Guide to the Food of Lollapalooza


A massive multi-stage music festival that takes place over four days in the middle of summer. The festival takes over Grant Park and dozens of bands perform. Expect a mix of household names and emerging acts to be on the lineup.

Concert and Movie Series

The Jay Pritzker Pavilion in Millennium Park hosts free movies and concerts in the summer. Packing a picnic and listening to the concert or watching the film are popular summertime activities for Chicago locals.

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Chicago gets pretty excited for summer. One of the many ways we celebrate summer is by launching fireworks every Wednesday and Saturday during the summer.

Chicago Blues Festival

A free blue festival in Millennium Park that attracts 500,000 attendees.

Chicago Gourmet Recap

Chicago Gourmet

A weekend food festival held in Millennium Park at the end of September. The event features wine tastings, food samples from Chicago restaurants, and cooking demonstrations from chefs.

Taste of Chicago

The world’s largest food festival takes place over five days in July in Grant Park. The main attraction is the food with dozens of Chicago restaurants participating but there is also live music.



A European-style Christmas Market that takes place on Daley Plaza between Thanksgiving and Christmas. There are stalls selling food, drinks, and gifts. It can be extremely crowded!

Dyeing the Chicago River Green

The Chicago River gets dyed a vibrant shade of green for St. Patrick’s Day. The event takes place at 8 am the Saturday before St. Patrick’s Day (or on St. Patrick’s Day if it falls on a Saturday). The river is dyed between Columbus and Wacker Drive. The color usually lasts a few days. This can be a rowdy and drunken event (yes, even at 8 am).

Where to Stay in Downtown Chicago

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Loews Hotel

Sure, it’s technically in River North but it’s so close to The Loop! I have stayed at this hotel before and I love it because it puts you in the middle of everything, yet the hotel itself feels so calm and quiet. The rooms are generous in size, and the rooftop bar/restaurant is a place to unwind surrounded by skyscrapers.

The Langham

A five star hotel that is considered one of the most luxurious places to stay in Chicago.

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The Blackstone

An Autograph Collection property across from Grant Park, this property manages to mix modern luxury with the history of the building. Many of the rooms have park views and the on-site restaurant is excellent.

Chicago Athletic Association Hotel

An affordable hotel in a Venetian Gothic style architectural landmark located across from Millennium Park. The aesthetic of the rooms was inspired by the building’s architecture and its history as a sports club.

Where to Eat and Drink in Downtown Chicago

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The LondonHouse rooftop has unbeatable views of the river and downtown Chicago. It’s a popular spot for happy hour and they do serve lunch and dinner. Reservations are available on Tock.

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City Winery

Located on the Riverwalk, this wine bar is open seasonally during warmer months. In the spring, heated domes keep patrons warm.

Gibson’s Italia

A three level Italian steakhouse on the Chicago River with a menu packed with seafood, steak, and housemade pasta options. This isn’t just any housemade pasta, its gold extruded pasta.


A rooftop bar with views of Grant Park, Millennium Park, and Lake Michigan. This is one of the best places to watch the fireworks on Wednesdays and Saturdays during the summer. The restaurant serves lunch, dinner, and weekend brunch and they do accept reservations. I love their brunch where items come in large family style portions.

RPM Seafood

The newest addition to the RPM empire, this large location is right on the Chicago River. The seafood centric menu has crudos and tartares, seafood towers, and a wide variety of seafood entrees. If seafood isn’t your thing, they menu also has steak and some other meat options.

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Mercat a la Planxa

This Spanish tapas restaurant by Chef Jose Garces is connected to The Blackstone Hotel, and it’s one of my go-to restaurants downtown. They serve classic tapas like croquetas, bacon wrapped dates, patatas bravas, padron peppers, and pan con tomate, plus entrees including paella, steak, and grilled iberico pork.

The Gage

This spot has the vibe of an elevated pub and it can be crowded after work. the menu has burgers and fish and chips plus steaks and lots of appetizers. they serve both lunch and dinner plus weekend brunch.

Cochon Volant

Cochon Volant

A French bistro with one of the best burgers in Chicago. This restaurant serves weekday breakfast and lunch, weekend brunch, plus nightly dinner. Dine on French classics like mussels frites, escargot, foie gras mousse, and steaks.

Beatnik on the River

A bar and restaurant brightly decorated in Moroccan and Indonesian furnishing. Beatnik on the River has outdoor seating with views of the river and a menu featuring creative cocktails and Mediterranean influenced food.

Food Halls in Downtown Chicago:


A food hall within Block 37 that serves Latin street food. Each food station focuses on something different. Try burgers, tacos, ceviche, sandwiches, or seafood. My favorite is the Chaufa Wok which is an ode to Peruvian-style stir fry – I order the Lomo Saltado.

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Revival Food Hall

Located at 125 South Clark Street, this food hall features 16 vendors representing cuisine from all over the globe. I love the buffalo chicken and truffle fries at Fat Shallot (pictured above) but you can also try poke, tacos, dosa, ramen, empanadas, burgers, pizza, fried chicken, and bbq. This food hall is open from 7 am to 7 pm and it can be crowded at lunchtime on weekdays.

Read More About Chicago:

What to do in Old Town
What to do in the West Loop
What to do in Wicker Park
What to do in the Gold Coast
What to do in River North
What to do in Downtown Chicago/The Loop
What to do in Lakeview
What to do in Streeterville

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