Things to Do in Chicago for Adults: Sip, Laugh, Tour, Dine, Dance

Chicago offers endless experiences for adults looking to enjoy the city’s vibrant culture and nightlife. Sip craft cocktails at rooftop bars with stunning skyline views or explore local breweries and wineries. Laugh out loud at famous comedy clubs like The Second City. Tour iconic landmarks, from the Chicago Riverwalk to architectural boat cruises. Dine at world-class restaurants, savoring deep-dish pizza, gourmet steaks, and global cuisine. Dance the night away at lively clubs, jazz lounges, or music festivals. Relaxation or adventure, Chicago has something unforgettable for every adult visitor.

Sip: Enjoy Chicago’s Best Drinks

Craft Cocktails at the Aviary – Chicago, USA

Aviary is a must-visit for cocktail lovers. This upscale bar, created by renowned chef Grant Achatz, serves innovative drinks that are more like an experience than a simple beverage. Try a cocktail served in a glass sphere or a smoky concoction that delights all senses.

Wine Tasting at City Winery – Various Locations, USA

For a more relaxed evening, visit City Winery in the West Loop. This urban winery offers an extensive selection of wines paired with delicious food. You can sit indoors or enjoy the outdoor patio while sipping on locally made wines.

Entry Fee:

Wine tastings typically range from $20 to $50+ per person, depending on the location and selection.
Special wine-pairing dinners and events may cost $75-$150+ per person.
Free entry to the venue, but reservations are recommended for tastings and concerts.

Activities:

Guided wine tastings featuring house-made and regional wines.
Wine and food pairings, including artisan cheeses and gourmet dishes.
Live music performances in a cozy, intimate setting.
Winemaking tours to learn about the production process.
Outdoor patio dining (varies by location).
Private event bookings for groups and celebrations.

Beer Tasting at Revolution Brewing

Craft beer lovers should head to Revolution Brewing, one of Chicago’s most popular breweries. Enjoy a flight of fresh brews, including their famous Anti-Hero IPA, while soaking in the lively atmosphere of their taproom.

Entry Fee:

Brewery tours and tastings start at $10-$20 per person, including a guided experience and beer samples.
Individual beer flights (samplers) range from $12-$18, depending on the selection.
Free entry to the Brewpub and Taproom, but food and drinks are paid separately.

Activities:

Guided brewery tours showcasing the brewing process (available at the Kedzie Taproom).
Beer tastings featuring Revolution’s flagship and seasonal brews.
Pairing experiences with craft beer and signature pub food.
Exclusive small-batch releases available only at the brewery.
Live events and community gatherings in the Taproom.
Merchandise shop for Revolution Brewing apparel and beer-to-go.

Rooftop Drinks at Cindy’s

Cindy’s, located atop the Chicago Athletic Association Hotel, offers stunning views of Millennium Park and Lake Michigan. Enjoy a handcrafted cocktail while watching the sunset over the city skyline.

Entry Fee:

No cover charge for entry.
Cocktails range from $15-$25.
Wine, beer, and food are available à la carte.

Activities:

Enjoy panoramic views of Millennium Park, Lake Michigan, and the Chicago skyline.
Sip craft cocktails, wine, and local beers in a chic rooftop setting.
Dine on seasonal dishes curated by expert chefs.
Relax in a stylish open-air terrace with a cozy firepit.
Attend special events and live DJ sessions on select nights.

Laugh: Catch a Comedy Show

The Second City

Chicago is known for its legendary comedy scene, and The Second City is where many famous comedians got their start. Catch an improv or sketch comedy show and enjoy an evening of laughter.

Entry Fee:

General admission tickets range from $25-$60+ per person, depending on the show and seating.
Premium and VIP seating options may cost more.
Special events and training center workshops have separate pricing.

Activities:

Watch world-class improv and comedy shows featuring talented performers.
Enjoy stand-up, sketch comedy, and musical performances.
Attend comedy workshops and improv classes at The Second City Training Center.
Dine and drink at the on-site bar while watching live performances.
Explore historic comedy memorabilia at the venue, which launched the careers of legends like Tina Fey and Steve Carell.

Zanies Comedy Club

Zanies is one of Chicago’s most iconic stand-up comedy clubs. Located in Old Town, this intimate venue hosts both local and national comedians who will have you laughing all night.

Entry Fee:

General admission tickets range from $20-$50+ per person, depending on the performer and seating.
A two-item minimum purchase (food or drinks) is required per person.

Activities:

Watch live stand-up comedy performances by local and national comedians.
Attend special events and themed comedy nights featuring rising and well-known comedians.
Enjoy a full bar with craft cocktails, beer, and wine.
Book VIP seating for a more intimate comedy experience.
Take part in open-mic nights or comedy workshops (occasionally offered).

Laugh Factory Chicago

Another great option for comedy lovers, the Laugh Factory in Lakeview features hilarious stand-up acts from rising stars and well-known performers.

Entry Fee:

General admission tickets range from $20-$50+ per person, depending on the show and performer.
A two-drink minimum is required per person.

Activities:

Watch live stand-up comedy featuring local, national, and celebrity comedians.
Enjoy themed comedy nights such as open-mic, LGBTQ+ showcases, and roast battles.
Sip cocktails, beer, and wine from the venue’s full-service bar.
Attend special events and comedy festivals.
Meet and interact with comedians after select shows.

Tour: Explore the City in Unique Ways

Architectural River Cruise

One of the best ways to experience Chicago’s stunning architecture is by taking a river cruise. The guided tour provides fascinating insights into the city’s skyline, famous buildings, and history while you relax on a boat.

Entry Fee:

Tickets range from $30-$60+ per person, depending on the cruise provider and time of day.
Premium or specialty cruises (sunset, cocktails) may cost more.

Activities:

Enjoy a guided tour of Chicago’s skyline with expert narration on the city’s architectural history.
Cruise along the Chicago River and see iconic landmarks like the Willis Tower, Wrigley Building, and Tribune Tower.
Learn about famous architects like Frank Lloyd Wright and Ludwig Mies van der Rohe.
Relax with food and drinks (available on select cruises).
Experience a sunset or evening cruise with illuminated city views.

Gangsters and Ghosts Tour

Step back in time and explore Chicago’s darker history with a Gangsters and Ghosts walking tour. Learn about the city’s Prohibition-era gangsters, haunted locations, and eerie legends.

Entry Fee:

Tickets range from $30-$45+ per person, depending on the time and date.

Activities:

Explore Chicago’s haunted history with expert guides.
Visit famous gangster-era locations tied to Al Capone, John Dillinger, and other notorious criminals.
Walk through haunted sites like the Palmer House, Congress Hotel, and Death Alley.
Learn about Prohibition-era crime, speakeasies, and ghost stories.
Enjoy a mix of history, mystery, and true crime storytelling.

Bobby’s Bike Hike

If you love staying active, a bike tour is a fun way to explore the city. Bobby’s Bike Hike offers guided tours that take you through famous neighborhoods, parks, and waterfront areas.

Entry Fee:

Bike tours range from $40-$80+ per person, depending on the type of tour.
Food and drink tours start at $60+ per person (includes samples).
Bike rentals available separately for $10-$15 per hour.

Activities:

Guided bike tours through Chicago’s top attractions, including Millennium Park and the Lakefront Trail.
Food tours featuring Chicago-style pizza, hot dogs, and local craft beer.
Night bike tours showcasing the city’s skyline and nightlife.
History and architecture rides covering famous landmarks.
Self-guided bike rentals for exploring at your own pace.

Chicago Food Tour

Taste your way through Chicago with a food tour. Try deep-dish pizza, Chicago-style hot dogs, Italian beef sandwiches, and more while learning about the city’s rich culinary history.

Entry Fee:

Tours range from $50-$100+ per person, depending on the provider and food inclusions.
Private and specialty tours may cost more.

Activities:

Taste iconic Chicago foods like deep-dish pizza, Chicago-style hot dogs, Italian beef, and Garrett Popcorn.
Explore famous neighborhoods such as River North, West Loop, and Chinatown.
Learn about Chicago’s food history from expert local guides.
Enjoy food and drink pairings on select tours.
Discover hidden gems and historic restaurants off the beaten path.

Dine: Savor the Best of Chicago’s Food Scene

Alinea

For an unforgettable fine dining experience, book a table at Alinea. This Michelin three-star restaurant offers a multi-course tasting menu with artistic and creative dishes.

Tasting menus start at $315+ per person (excluding drinks, tax, and gratuity).
Wine pairings available for an additional cost.
Reservations required (often booked months in advance).

Activities:

Experience a world-renowned, three-Michelin-starred dining adventure.
Enjoy a multi-course tasting menu featuring molecular gastronomy and artistic plating.
Engage in an immersive dining experience with interactive dishes and unique presentations.
Choose from different dining options:
- The Gallery: A theatrical, multi-sensory experience.
- The Salon: A refined tasting menu experience.
- The Kitchen Table: A private, chef-curated meal for an exclusive group.

Gibsons Bar & Steakhouse

A Chicago classic, Gibsons is the place to go for a juicy steak. Located in the Gold Coast neighborhood, this famous steakhouse serves high-quality meats and classic cocktails in an elegant setting.

Girl & The Goat

For a trendy and lively dining experience, try Girl & The Goat. Chef Stephanie Izard’s restaurant is known for its bold flavors and creative small plates.

Lou Malnati’s Pizzeria

No trip to Chicago is complete without deep-dish pizza, and Lou Malnati’s is one of the best places to try it. Their buttery crust, rich tomato sauce, and gooey cheese make it a must-try.

Dance: Experience Chicago’s Nightlife

Smart Bar

If you love electronic music and a fun crowd, Smart Bar in Wrigleyville is a top choice. This underground club features top DJs spinning house and techno beats.

Tao Chicago

For a more upscale nightlife experience, head to Tao Chicago. This club and restaurant offer a luxurious setting, live DJs, and an energetic dance floor.

The Hideout

For a unique and intimate venue, The Hideout is a great choice. This small bar hosts live music and dance nights, with a friendly and relaxed vibe.

Untitled Supper Club

This speakeasy-style club combines live jazz, burlesque performances, and a lively dance floor. It’s a great spot for those looking to enjoy live entertainment while sipping on craft cocktails.

Chicago offers endless entertainment for adults looking to sip, laugh, tour, dine, and dance. Whether you want a relaxing evening with drinks, an exciting comedy show, a fascinating city tour, an unforgettable meal, or a fun night out dancing, the city has something to offer. Plan your visit and experience the best of Chicago’s vibrant nightlife and cultural scene.

FAQs

What is the most famous attraction in Chicago?

Millennium Park, home to Cloud Gate (The Bean), is a must-visit.

Where can I get the best skyline views in Chicago?

Visit Willis Tower Skydeck or 360 Chicago at the John Hancock Center.

What is a fun place to visit with kids in Chicago?

The Shedd Aquarium offers amazing marine life exhibits.

Where can I enjoy a scenic waterfront experience?

Navy Pier features rides, restaurants, and stunning lake views.

What’s a must-see museum in Chicago?

Art Institute of Chicago is world-famous for its art collections.

Where can I explore Chicago’s history and science?

The Field Museum offers fascinating dinosaur and historical exhibits.

What’s a great place for outdoor activities in Chicago?

Chicago Riverwalk is perfect for walking, dining, and boat tours.

Where can I enjoy nature in Chicago?

Lincoln Park Zoo is a free and beautiful spot to explore wildlife.

What’s a top shopping destination in Chicago?

The Magnificent Mile is the best place for shopping and dining.

Where can I experience Chicago’s nightlife?

River North is packed with lively bars, clubs, and rooftop lounges.

Things to Do in Chicago for Adults: Sip, Laugh, Tour, Dine, Dance

Sip: Enjoy Chicago’s Best Drinks

Craft Cocktails at the Aviary – Chicago, USA

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