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Guide to the Loop

Fun activities with scenic views

Made for those who want to fill their schedule with engaging activities but refuse to do so without a constant, sweeping view of the city.

Based on 825 Opinions
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Updated May 2026
01
Grant Park image 1
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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.

Stunning views of the Chicago skyline and Lake Michigan dominate the scene. Vantage points offer breathtaking lake views and a peaceful backdrop for biking or reflection.

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.

People are saying

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

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

"I loved the beautiful skyline and lake views."

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.

Views of downtown shine through large windows, filling the space with natural light. Climbing areas offer awesome cityscapes that add to the experience.

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

People are saying

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

"The route setting here is fun and challenging."

"I loved the awesome city views while climbing."

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.

Stunning views of Chicago's skyline and Lake Michigan dominate the scene. Indoor/outdoor dining overlooks Michigan Avenue, adding to the breathtaking experience with a gorgeous building backdrop.

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

People are saying

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

"The scenic views of Lake Michigan are beautiful from here."

"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.

Great views come with several free seating areas to relax. An audio display enhances the viewing experience.

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.

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.

Gorgeous views dominate the scene with beautiful cityscapes visible from the plaza. The spot offers a clear and open vantage point perfect for taking in the surroundings.

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.

People are saying

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

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

"The scenic views here are beautiful and gorgeous."

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 here offers incredible city views, especially at night. The skyline and lake create a stunning backdrop from the ice skating ribbon and park areas.

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.

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 from the skating ribbon 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.

Seats above the back of the stage offer a unique view and an unusual way to experience the symphony. The highest balcony provides an amazing perspective, with breathtaking views inside and outside the building.

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

People are saying

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

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

"The scenic views from the highest balcony were amazing."

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
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.

Great views come from every seat, including the loge, balcony, and dress circle. Even the upper balcony and nosebleed seats offer a clear perspective of the stage.

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

People are saying

"The theater is gorgeous and beautifully ornate."

"The seats here are really comfortable."

"The views from almost every seat were great."

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.

09
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.

Seating offers a gorgeous view of the skating rink. The view from the restaurant overlooks the ice rink clearly and adds to the dining experience.

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.

People are saying

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

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

"The scenic views of the ice rink were amazing."

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.

10
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.

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.

11
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.

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

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.

People are saying

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

"The scenic views from the room were breathtaking."

"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.

12
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.

Seating by the window offers a perfect view of the Muddy Waters mural. Windows also showcase interesting views and a holiday tree decorated in Marshall Fieldโ€™s colors.

People are saying

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

"The food here is delicious and full of flavor."

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

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.

13
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.

Big windows offer mesmerizing city views that you can enjoy from upstairs seating or inside. The atmosphere highlights the pleasant street scenes visible through the windows.

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

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 city views 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.

14
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.

Smaller venue size offers good views from every seat. Some seats on the balcony have pillars or speakers blocking side views, so seating choice matters.

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

People are saying

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

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

"The interior is absolutely beautiful and historic."

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.

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.

Views include a beautiful downtown skyline and the Institute of Modern Art. Michigan Avenue offers a nice atmosphere with pleasant sights.

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.

People are saying

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

"I found the scenic views to be beautiful and amazing."

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

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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