Last updated on October 19th, 2025
From thrilling entertainment venues to serene natural escapes, Rosemont offers an incredible variety of activities just minutes from downtown Chicago. Whether you’re visiting for a convention, a concert, or a weekend getaway, these top things to do in Rosemont blend world-class entertainment with local charm. Discover why this vibrant suburb is one of Illinois’ premier destinations for fun and exploration.
Here are the best things to do in Rosemont for an unforgettable experience in the Chicago area.
Why Visit Rosemont?
Rosemont’s prime location offers:
🎭 World-class entertainment venues
🛍️ Premier shopping and dining
🎪 Unique local attractions and events
🚇 Easy access to downtown Chicago
🌳 Beautiful parks and natural areas
Best Things to Do in Rosemont
1. Rosemont Theatre
The Rosemont Theatre is a premier entertainment venue hosting Broadway shows, concerts, comedy acts, and special events. With its excellent acoustics and comfortable seating, this 4,200-seat theater provides an intimate experience for enjoying world-class performances. Catching a show here is one of the top things to do in Rosemont for culture enthusiasts.
- Highlights: Broadway productions, concert series, comedy shows
- Perfect for: Theater lovers and entertainment seekers
- Location: 5400 N River Rd, Rosemont, IL 60018
2. Chicago Architecture River Cruise
Experience Chicago’s legendary architecture from the best vantage point—the river. The Chicago Architecture River Cruise offers breathtaking views of skyscrapers and historical landmarks while expert guides share fascinating stories about the city’s architectural heritage. This is undoubtedly one of the most educational and scenic things to do in Rosemont and the surrounding Chicago area.
- Highlights: Expert narration, iconic skyscraper views, photo opportunities
- Perfect for: Architecture enthusiasts and first-time visitors
- Duration: Approximately 90 minutes
3. Allstate Arena
The Allstate Arena is one of the Midwest’s premier entertainment venues, hosting major concerts, sporting events, and family shows. With a capacity of over 18,000, this versatile arena brings top-name performers and exciting events to Rosemont throughout the year. Attending an event here is definitely one of the most exciting things to do in Rosemont for sports and music fans.
- Highlights: Major concerts, Chicago Wolves hockey, family shows
- Perfect for: Sports fans and concert-goers
- Location: 6920 N Mannheim Rd, Rosemont, IL 60018
4. Chicago Favorites Ultimate Food and Walking Tour
Discover Chicago’s culinary delights with the Chicago Favorites Ultimate Food and Walking Tour. This guided experience takes you through the city’s diverse neighborhoods to sample iconic dishes like deep-dish pizza, Chicago-style hot dogs, and other local specialties while learning about the city’s history and architecture. It’s one of the most delicious things to do in Rosemont’s neighboring Chicago areas.
- Highlights: Deep-dish pizza, Chicago-style hot dogs, neighborhood exploration
- Perfect for: Foodies and cultural explorers
- Duration: Approximately 3 hours
5. Donald E. Stephens Convention Center
The Donald E. Stephens Convention Center is one of the nation’s premier convention facilities, hosting major trade shows, conferences, and consumer events throughout the year. With over 840,000 square feet of exhibit space and state-of-the-art facilities, this center attracts visitors from around the world. Exploring the various events here offers some of the most interesting things to do in Rosemont for business travelers and curious visitors alike.
- Highlights: Major trade shows, comic conventions, consumer expos
- Perfect for: Business travelers and event enthusiasts
- Location: 5555 N River Rd, Rosemont, IL 60018
6. Chicago Lincoln Park Indoor Skydiving with Two Flights
Experience the thrill of skydiving without jumping from a plane at Chicago Lincoln Park Indoor Skydiving. This state-of-the-art vertical wind tunnel lets you float on a column of air, experiencing the sensation of freefall in a safe, controlled environment. With two flights included, you’ll have plenty of time to master the basics and enjoy this adrenaline-pumping activity. It’s one of the most thrilling things to do in Rosemont and the surrounding Chicago area.
- Highlights: Safe skydiving simulation, professional instruction, adrenaline rush
- Perfect for: Adventure seekers and thrill enthusiasts
- Duration: Approximately 1-2 hours
7. Wolff’s Flea Market – Rosemont
Wolff’s Flea Market in Rosemont is a treasure hunter’s paradise, featuring hundreds of vendors selling everything from antiques and collectibles to new merchandise and fresh produce. Open year-round on weekends, this massive market offers a fun shopping experience where you can find unique items, bargain deals, and local specialties. Browsing through Wolff’s is one of the most enjoyable things to do in Rosemont for shoppers and families.
- Highlights: Antiques, collectibles, fresh produce, bargain shopping
- Perfect for: Treasure hunters and bargain shoppers
- Hours: Weekends, year-round
8. Trickery Chicago Magic Show
Experience wonder and amazement at the Trickery Chicago Magic Show, featuring world-class magicians performing mind-bending illusions, sleight of hand, and interactive magic in an intimate setting. This professional magic show offers entertainment that delights both adults and children, making it one of the most magical things to do in Rosemont and the Chicago area for families and couples.
- Highlights: Close-up magic, audience participation, professional illusionists
- Perfect for: Families, date nights, and magic enthusiasts
- Duration: Approximately 90 minutes
9. Pete’s Dueling Piano Bar
Pete’s Dueling Piano Bar offers an unforgettable night of entertainment where talented musicians battle it out on twin pianos, taking requests and getting the whole crowd singing along. This interactive experience combines music, comedy, and audience participation for a lively evening that’s perfect for groups, birthdays, or just a fun night out. It’s definitely one of the most entertaining things to do in Rosemont for adults.
- Highlights: Live music requests, audience participation, full bar
- Perfect for: Groups, celebrations, and music lovers
- Hours: Nightly entertainment
10. Chicago Architecture Center River Cruise aboard First Lady
The Chicago Architecture Center River Cruise aboard First Lady offers a premium architectural tour experience with expert docents from the Chicago Architecture Center. This 90-minute cruise provides in-depth commentary on Chicago’s famous skyline, historic buildings, and architectural innovations while you relax on the comfortable First Lady vessel. It’s one of the most educational and scenic things to do in Rosemont’s neighboring Chicago area.
- Highlights: Expert architectural guides, comfortable seating, comprehensive commentary
- Perfect for: Architecture enthusiasts and history buffs
- Duration: 90 minutes
11. Chicago Crime and Mob Bus Tour
Delve into Chicago’s notorious criminal history with the Chicago Crime and Mob Bus Tour. This fascinating guided tour takes you to infamous locations associated with Al Capone, John Dillinger, and other legendary gangsters while expert guides share gripping stories about Chicago’s underworld history. It’s one of the most intriguing things to do in Rosemont’s surrounding area for history enthusiasts and true crime fans.
- Highlights: Gangster history, famous crime scenes, expert storytelling
- Perfect for: History buffs and true crime enthusiasts
- Duration: Approximately 2 hours
12. Joe’s Live
Joe’s Live is Rosemont’s premier live music venue, featuring national touring acts, local bands, and comedy shows in an intimate setting. With excellent acoustics, a full menu, and craft cocktails, this venue offers a sophisticated nightlife experience. Catching a show here is one of the best things to do in Rosemont for music lovers seeking quality entertainment.
- Highlights: Intimate concerts, comedy shows, full restaurant and bar
- Perfect for: Music enthusiasts and date nights
- Location: 5441 Park Place, Rosemont, IL 60018
13. Flyover in Chicago
Experience the thrill of flight without leaving the ground at Flyover in Chicago. This state-of-the-art flight simulation ride takes you on a breathtaking journey over Chicago’s iconic landmarks and natural wonders using cutting-edge technology, wind effects, and motion seating. It’s one of the most immersive and exciting things to do in Rosemont and the Chicago area for adventure seekers of all ages.
- Highlights: Virtual flight experience, motion simulation, wind effects
- Perfect for: Families and adventure seekers
- Duration: Approximately 30 minutes
14. The Muscle Car and Corvette Nationals
Automotive enthusiasts won’t want to miss The Muscle Car and Corvette Nationals, one of the nation’s premier classic car shows held annually in Rosemont. This spectacular event features hundreds of pristine muscle cars, rare Corvettes, and automotive memorabilia, drawing collectors and fans from across the country. Attending this show is one of the most exciting things to do in Rosemont for car lovers.
- Highlights: Rare muscle cars, vintage Corvettes, automotive history
- Perfect for: Car enthusiasts and collectors
- When: Annual November event
15. Chicago Craft Brewery Barrel Bus Tour
Hop aboard the Chicago Craft Brewery Barrel Bus Tour for a fun-filled journey through Chicago’s vibrant craft beer scene. This guided tour takes you to multiple local breweries where you can sample unique beers, learn about the brewing process, and enjoy behind-the-scenes access. It’s one of the most enjoyable things to do in Rosemont’s surrounding area for beer enthusiasts and social groups.
- Highlights: Multiple brewery visits, beer tastings, behind-the-scenes access
- Perfect for: Beer lovers and social groups
- Duration: Approximately 3-4 hours
16. Dunne Park Recreation Center
The Dunne Park Recreation Center offers a wide range of recreational activities and facilities for all ages. From fitness classes and sports leagues to community events and swimming pools, this center provides numerous opportunities for active fun and social engagement. Visiting Dunne Park is one of the best things to do in Rosemont for families and fitness enthusiasts.
- Highlights: Swimming pools, fitness classes, sports facilities, community events
- Perfect for: Families and active individuals
- Location: 6100 S Ruby St, Rosemont, IL 60018
17. Chicago Sightseeing River and Lake Cruise
Combine river and lake perspectives with the Chicago Sightseeing River and Lake Cruise. This comprehensive tour takes you through the Chicago River’s architectural canyon and out onto Lake Michigan for stunning skyline views from the water. The dual perspective offers a complete Chicago experience, making it one of the most comprehensive things to do in Rosemont’s neighboring area for sightseers.
- Highlights: Architectural river tour, lake skyline views, comprehensive commentary
- Perfect for: First-time visitors and photography enthusiasts
- Duration: Approximately 90 minutes
18. Catherine Chevalier Woods
Escape to nature at Catherine Chevalier Woods, a beautiful forest preserve offering hiking trails, picnic areas, and peaceful natural surroundings just minutes from Rosemont. This 240-acre preserve features diverse habitats, wildlife viewing opportunities, and seasonal beauty that provides a perfect contrast to the urban excitement of the area. Exploring these woods is one of the most relaxing things to do in Rosemont for nature lovers.
- Highlights: Hiking trails, bird watching, picnic areas, natural beauty
- Perfect for: Nature enthusiasts and families
- Location: Higgins Rd, between River Rd and Cumberland Ave
FAQs About Things to Do in Rosemont
Final Tips for Visiting Rosemont
– Check event calendars for Rosemont Theatre and Allstate Arena before your visit
– Use public transportation – Rosemont is served by the CTA Blue Line
– Combine activities – many attractions are within walking distance of each other
– Book tours in advance during peak seasons
Whether you’re seeking world-class entertainment, unique tours, or relaxing natural escapes, Rosemont offers an incredible variety of activities that complement the broader Chicago experience. From thrilling adventures to cultural enrichment, these things to do in Rosemont promise memorable experiences for every type of traveler.
