13+ experiences available
Chicago
The city that works — and plays harder
Deep dish, deep house, deep culture. From Lollapalooza to legendary jazz clubs, Chicago brings world-class nightlife with Midwest heart.
1
Trip Packages
12
Upcoming Events
20
Venues
Featured Stories in Chicago
Best Restaurants Near Soldier Field for R&B Tour Weekend
Where to eat before and after the Usher and Chris Brown show at Soldier Field on August 21, 2026. Pre-show dinner spots, late-night eats, and next-day brunch.
Read
Where to Party After Usher and Chris Brown in Chicago
The R&B Tour hits Soldier Field on August 21, 2026. Here is where the party continues in River North and South Loop and beyond.
Read
The R&B Tour in Chicago: Your Complete Travel Guide
Everything you need to know about Usher and Chris Brown's R&B Tour stop at Soldier Field on August 21, 2026. Hotels, dining, nightlife, and the full weekend plan.
Read
Chicago White Sox Opening Day 2027: Guaranteed Rate Field and the South Side
Your complete guide to White Sox Opening Day 2027 at Guaranteed Rate Field, from Bridgeport tailgates to Armour Square neighborhood eats.
ReadFeatured Venues in Chicago
Featured Ambassadors in Chicago
This spot is open. Top ambassadors earning commissions in Chicago get featured here — it's how travelers find the locals they trust.
Upcoming Events
Fri, Jul 10
Drunk Shakespeare: Drunk Romeo & Juliet (21+ Event)
Fri, Jul 10
Chris Lake
Fri, Jul 10
Hard Country Honky Tonk with The Hoyle Brothers
Fri, Jul 10
The Second City's: Pandemonium, Please Hold
Fri, Jul 10
Chicago White Sox vs. Athletics
Fri, Jul 10
Balloon Museum | EmotionAir - Art You Can Feel - Chicago
Fri, Jul 10
Classic Stadium Tour
Fri, Jul 10
Windy City Smokeout
Latest from Chicago
View all articles →
Balloon Museum EmotionAir Chicago: Art You Can Feel in 2026
Experience Balloon Museum's EmotionAir in Chicago on July 10, 2026 — an immersive art exhibition that turns inflatable wonder into emotional connection.
Read More
Chicago White Sox vs. Boston Red Sox: July 2026 Game Guide
Catch the Chicago White Sox take on the Boston Red Sox on July 9, 2026. Here is everything you need to know before game day.
Read More
Going Bacharach: The Songs of An Icon Live in the City
Experience Going Bacharach: The Songs of An Icon live on July 8, 2026. A must-attend night celebrating the timeless music of a legendary composer.
Read More
Balloon Museum EmotionAir Chicago 2026 - Immersive Art Experience
Experience EmotionAir at Balloon Museum Chicago June 15, 2026. Immerse yourself in interactive art installations that transform spaces into emotional journeys.
Read More
A Dog's House June 14, 2026 - Premier Event in The City
Experience A Dog's House at a premier venue on June 14, 2026. Get ready for an unforgettable night in the city's hottest destination.
Read More
Going Bacharach: The Songs of An Icon in the city - June 2026
Experience the timeless melodies of Burt Bacharach at this special tribute event in the city on June 13, 2026. A night of classic songbook magic awaits.
Read More
Get the Chicago Weekend Guide
The best events, restaurants, and experiences in Chicago — delivered every Thursday.
No spam. Unsubscribe anytime.
Ready to experience Chicago?
Browse our curated packages or request a custom trip designed just for you.