Hand-picked deals by our pirate team
Get inspired!
Hand-picked deals by our pirate team
Hand-picked deals by our pirate team
Get inspired!
Hand-picked deals by our pirate team
👨🍳 Say "Yes, Chef!" To A Weekend In Chicago!
Slice 15+% off these fantastic weekend vacays to the Windy City!
From $383
Fly to Chicago for a weekend tasting all that this great American city has to offer!
Enjoy the Hyatt Place Downtown/The Loop (4.5/5 on TripAdvisor) spacious rooms, prime location and comfy digs before diving into the Windy City's vibrant music and foodie scene. Explore Millennium Park, marvel at the Art Institute, and shop the Magnificent Mile. Or enjoy local staples like deep-dish, Chicago hot dogs and some of the country's top restaurants!
These weekend vacations also include roundtrip - often nonstop - flights with Frontier, Spirit and others!
Highlights
Departure
- New Orleans
- Philadelphia
- Dallas
- Portland
- Boston
- Atlanta
- Washington
- Las Vegas
- New York City
Destination
- Chicago
Details
Here are some of the dates and departure airports we found for you, but there are many more available.
Here's the cheapest deal we found...
Additional Information
All of our deals are available at the time of publishing, but prices are subject to fluctuate and change at any time.
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