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New Yorkers 1st Choice
Loved by locals

Fun activities with nice views in the Loop

A moment to step back and take in the skyline while staying active. The city looks different when you are actually doing something.

Based on 801 Opinions
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Updated May 2026
01
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City park

Urban park offers panoramic city skyline views and a huge central fountain surrounded by spacious green lawns and walking paths. Atmosphere balances peaceful lakeshore relaxation with lively areas like a skatepark and playground. Frequent events and live entertainment bring diverse crowds together in a vibrant yet calm setting.

Lots of walking and sights keep things interesting. Festivals add extra layers of Summertime fun and the space offers a calming spot to relax with family.

Spectacular views of the Chicago skyline and Lake Michigan dominate the scene. Scenic spots overlook the beach and Buckingham Fountain, creating a peaceful and beautiful backdrop.

People are saying

"It's a beautiful, spacious park with great walking trails."

"I loved the nice view of the skyline and lake."

"I found the festivals and concerts here to be a ton of fun."

Good to know

1

Parking costs $30 per day near Grant Park.

2

Public restrooms are not available in Grant Park.

3

Consider using Uber or bus transportation when visiting Grant Park.

02
First Ascent Block 37 image 1
Rock climbing gym

Spacious rock climbing gym with incredible downtown views and varied bouldering problems across many walls. Atmosphere stays friendly and welcoming, serving as a social and relaxing third space. Amenities include a large fitness area, yoga classes, and free keypad lockers, enhancing the overall experience.

Bouldering offers a fun environment with challenging problems set by skilled routesetters. The gym suits both beginners and those seeking an intense workout.

Views of downtown and the city stand out with natural light flooding the space. The weight room and climbing areas both offer awesome cityscapes that add to the experience.

People are saying

"The climbing gym's setting is the best in the city, forcing technique."

"The staff at this rock climbing gym are so friendly and helpful."

"The route setting here is fun and challenging."

Good to know

1

The gym opens until 11pm, but the mall closes at 10pm.

2

A daily pass costs $33, which may be high for new climbers.

3

New climbing routes are set approximately twice a week.

03
University Club of Chicago image 1

Building showcases early 20th century architecture with historic character and beautiful views. Atmosphere blends classy, elegant charm with modern exclusivity, creating a harmonious and inviting setting. Amenities include squash courts, gym, library, and bar, supporting both relaxation and active pursuits.

Tremendously fun atmosphere with a crowd that adds to the lively vibe. The setting encourages staying and enjoying various activities.

Stunning views of Chicago's skyline and Lake Michigan dominate the scene. An indoor/outdoor dining room overlooks Michigan Avenue, adding to the breathtaking views and old school atmosphere.

People are saying

"The views of Lake Michigan from the club are great."

"This historic building is fascinating and stunning."

"The views of Lake Michigan from the 7th floor are amazing."

Good to know

1

The club hosts various events, including weddings and corporate gatherings.

2

Expect high costs for events, with weddings starting around $50,000.

3

Reservations are recommended for dining, especially during peak hours.

04
The Jetty | Riverwalk image 1

Riverwalk offers great views along the water with outdoor seating and playground areas for families. The atmosphere shifts from calm during the day to a different vibe at night, with plenty of food options nearby. Dogs and people enjoy walking and relaxing in this clean, well-secured space.

The spot offers fun activities perfect for picnics with family and friends. The Jetty and Riverwalk provide a lively setting that keeps the experience engaging and enjoyable.

Several free areas offer spots to sit and take in the great views along the riverwalk. The setting combines scenic views with nearby activities for a pleasant experience.

People are saying

"I enjoyed the great views and walking around."

"I loved watching the boats and human life go by."

"The views here are great and good."

Good to know

1

The Jetty is the best place to view the display because it has audio.

2

You can walk, kayak, or take a boat ride there.

3

There are several 'free areas' to sit and enjoy the view.

05
McCormick Tribune Plaza image 1
Ice skating rink

Ice skating rink sits under a large chrome sculpture, offering spacious ice surface and gorgeous city views. Music plays through loudspeakers, creating an energetic atmosphere that suits both beginners and advanced skaters. Evening lighting enhances the photogenic setting, making it a popular spot for skating and socializing.

Evenings bring out the most fun atmosphere with lights enhancing the surroundings. The rink offers a good spot for pictures and fun, though security measures fall short.

Skating here puts you right in the middle of beautiful scenery. The gorgeous views at the plaza add a great backdrop to the experience.

People are saying

"I loved skating in the heart of these parks surrounded by beautiful scenery."

"The views here are gorgeous and make for a beautiful skating experience."

"It's a fantastic ice skating rink for fun activities."

Good to know

1

The ice skating rink is free to enter, but renting skates costs $20.

2

Ice skating is open from mid-November through mid-March.

3

Public restrooms are available on site for visitors.

06
Maggie Daley Park Ice Skating Ribbon image 1

Ice skating ribbon features a unique track shape with varying elevations that create a more fun experience than typical oval rinks. Skating offers amazing city skyline views and a vibe that feels like skating on a river in the woods. The atmosphere is lively with music and crowds, especially during evening sessions when city lights enhance the scenery.

Skating on the ribbon-shaped ice rink offers a unique experience with its varying elevations and more space than typical rinks. Both beginners and seasoned skaters find it a fun and engaging activity.

Views of the city skyline and lake stand out, especially from the ice skating ribbon. Skating here offers stunning cityscapes and a unique perspective of downtown and the surrounding buildings.

People are saying

"The ice skating ribbon offers a fun, unique experience with slopes."

"The ice skating ribbon at these parks feels like skating on a river in the woods."

"The city skyline views while skating are incredible."

Good to know

1

Reservations are required in advance as time slots fill up quickly.

2

Ice skating is available from mid-November through mid-March.

3

The park has two entrances, one with lockers and restrooms.

07
Chicago Symphony Orchestra image 1

Symphony Hall offers exceptional acoustics and an intimate setting with beautiful historic architecture. Performances feature world-class musicians delivering clear, balanced sound throughout the venue. The atmosphere is classy and professional, creating a refined experience for classical music lovers.

Interactive performances combine nostalgia and musicianship, creating a lively atmosphere. Additional fun activities after shows keep the energy going.

Views from the highest balcony and box seats offer amazing sights and great sound. Windows provide breathtaking views inside and outside, capturing that Chicago vibe.

People are saying

"The Symphony's performance was truly wonderful and amazing."

"The kids' programming with costumes and storytelling was fantastic."

"The fun activities here are a memorable, interactive experience."

Good to know

1

Children's concerts are interactive and educational, perfect for family outings.

2

Arrive at least 15 minutes early to ensure seating for performances.

3

The venue hosts movie concerts, enhancing the experience with live orchestral music.

08
Millennium Hall Restaurant image 1

Architecture features Frank Gehry's dancing metal design with indoor and outdoor seating offering views of the ice rink and cityscape. Atmosphere ranges from festive and chill to lively with large projection TVs showing sports. Popular for group outings and casual dining with a bar-focused vibe.

Chef David leads with knowledge and passion, making the pizza-making lesson both fun and approachable. The experience includes pizza, drinks, an appetizer, and clear instruction, creating a great group activity.

Seating offers a gorgeous view of the skating rink. Dining overlooks Millennium Hall, providing a nice visual backdrop.

People are saying

"Chef David's pizza making class was so fun and awesome."

"Chef David made the pizza-making experience fun and unforgettable."

"I enjoyed the nice view from the restaurant."

Good to know

1

Reservations are recommended for pizza-making courses and private events.

2

Happy hour runs from 4-6pm with discounted drinks and appetizers.

3

Karaoke night starts at 10pm on Thursdays with a two-drink minimum.

09
Auditorium Theatre image 1
Performing arts theater

Auditorium Theatre offers historic architecture with ornate design and classic ambiance that transports visitors back in time. The space fills with rich acoustics that enhance live performances, creating a magical atmosphere. Comfortable seating and a mix of old charm with modern touches define the experience.

Fascinating tours highlight the theatre's beauty and add to the fun. Shared boxes seat four with friendly guests enhancing the experience.

Fantastic views come from the front section of the lower balcony and the top balcony offers a good view of the stage. All seats provide a solid view throughout the auditorium.

People are saying

"It's a beautiful, historic venue for performing arts."

"It's a beautiful and historic venue with a stunning interior."

"The historic vibe here is beautiful and adds to the experience."

Good to know

1

Parking is a pay lot right across the street from the theatre.

2

Expect seating issues due to pillars blocking views in some areas.

3

The show starts at 7pm; arrive early for best seating.

10
theWit Chicago, a Hilton Hotel image 1

Hotel offers lively rooftop bar with great city views and vibrant atmosphere. Rooms and common areas feature funky artwork and a comfy, eclectic design. Nighttime brings street noise and energetic crowds, especially near the club and light rail.

A rooftop bar offers a lively spot with a large dance floor and friendly staff. Events include themed celebrations and fundraisers with activities like roof repelling, adding to the fun atmosphere.

Rooms offer amazing city and river views, with many featuring scenic sights. The rooftop bar also provides a great spot for panoramic views.

People are saying

"The hotel's five-star service made my day better."

"The views from the rooms were breathtaking and amazing."

"The rooftop bar was really fun with a great city view."

Good to know

1

The rooftop bar hosts a brunch buffet on weekends.

2

Private events frequently close the rooftop bar, limiting access.

3

Valet service is recommended as there is no parking available.

11
James M. Nederlander Theatre image 1
Performing arts theater

Performing arts theater showcases 1920s art deco decor and gorgeous interior with comfortable seating and great stage views. Atmosphere feels breathtaking and grand, creating an unforgettable experience with incredible sound. Exclusive suite service offers private lounge with drinks and snacks, enhancing the overall visit.

Stage effects and magic illusions create an entertaining and fun atmosphere. Photo opportunities and casual dress add a playful touch to the experience.

Views come from almost every seat, including the balcony and the Dress Circle. Even seats in the second to last row upstairs offer a clear sightline with nothing blocking the view.

People are saying

"The theater is gorgeous and beautifully ornate."

"The seats here are really comfortable."

"The balcony seats offer a nice view from almost every spot."

Good to know

1

Parking is available in a garage just around the corner from the theater.

2

Expect long lines for the restrooms during intermission; plan accordingly.

3

The balcony seats provide great views and are less expensive than front-row seats.

12
Chicago Athletic Association - The Unbound Collection by Hyatt image 1

Venetian-Gothic architecture shapes a stylish hotel with ornate woodwork and intricate carvings. Lively atmosphere fills public game rooms and a rooftop bar with great views of the lake and park. Athletic-themed amenities include basketball, bocce, and yoga, blending historic charm with active recreation.

Rooftop offers a spectacular view. Rooms on the 7th floor overlook Millennium Park with excellent views and comfortable amenities.

People are saying

"It's a striking historical site with authentic charm and artistic details."

"The rooftop bar has an awesome view of Millennium Park."

"The game room is a fun spot for drinks and games like chess or pool."

Good to know

1

Happy hour runs daily from 4-6pm with discounted drinks.

2

Expect wedding crowds on weekends due to the hotel's wedding venue status.

3

Reservations are required weeks in advance for dinner at Cindy's Rooftop.

13
The Walnut Room image 1
American restaurant

Dining room showcases historic decor and a stunning Christmas tree that creates a magical atmosphere. Fairy princesses visit tables, adding a whimsical touch to the experience. Space feels spacious and elegant with white tablecloths and a sense of Chicago history.

Windows offer interesting views including a Muddy Waters mural. A holiday tree decorated in Marshall Fieldโ€™s colors adds to the scene.

People are saying

"The holiday atmosphere and the Great Tree are just stunningly gorgeous."

"The Christmas tree here is magnificent and makes for a festive vibe."

"The Christmas tree makes for a really nice view."

Good to know

1

Reservations are required for holiday dining at least two months in advance.

2

The Walnut Room hosts a popular drag brunch every Sunday at 11 AM.

3

Parking costs $28 for three hours, so plan accordingly.

14
Nutella Cafe Chicago image 1

Nutella-themed decor creates a bright and inviting space with personalized Nutella jars as a unique feature. The cafe feels cramped and crowded, with small tables placed very close together, often leading to a noisy atmosphere. Outdoor patio seating offers an alternative to the tight indoor space.

Colorful menu items and customized Nutella jars create a playful atmosphere. Kids enjoy hot chocolate and the chance to take home personalized souvenirs.

Big windows offer mesmerizing city views that fill the space with light. Seating upstairs provides a pleasant vantage point to enjoy the streets and skyline.

People are saying

"You have to try the Nutella Crepe with bananas; it's very tasty."

"It's a fun experience for Nutella lovers satisfying sweet cravings."

"I loved the nice view of the city from the big windows."

Good to know

1

Expect a wait time of 30-45 minutes during peak hours.

2

The cafe opens at 8 am daily.

3

You can personalize your Nutella with your name for a unique souvenir.

15
Sugary Chicago image 1
Brunch restaurant

Bright, Instagrammable design with beautiful views of downtown and nearby parks creates a warm, fun atmosphere. Music plays loudly, adding energy but sometimes overwhelming the space. Small size and close seating make the environment feel cozy yet busy.

Fun here comes with a touristy vibe and moments that feel festive. Roberto adds to the experience with his patience, fun attitude, and great photos.

Views include downtown skyline and the Institute of Modern Art, creating a beautiful atmosphere. Outdoor seating features umbrellas near a park setting.

People are saying

"I enjoyed the breakfast; the food was special and delicious."

"The menu's loose pages made for a chaotic, adventurous dining experience."

"I found the view here to be beautiful and amazing."

Good to know

1

A $30 seating charge applies to all tables.

2

A service fee is added for large parties of more than two people.

3

Reservations are not honored; it's first come, first served.

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