Hand-picked deals by our pirate team
Get inspired!
Hand-picked deals by our pirate team
4⭐️ Chicago Weekend Getaway from Under $150 🤯🙌
Luxe Chicago Weekend Trip from $139 Including an Award-Winning Hilton Hotel & Flights!
From $139
We've found a fabulous Chicago weekend getaway for budget weekday prices! Fly out from Friday to Sunday and spend two nights at the 4-star Canopy by Hilton Chicago Central Loop (4.5/5 on TripAdvisor & winner of the 2023 Travelers' Choice Award), where you'll enjoy a prime location, stylish decor, and a cocktail bar.
While you'd typically pay at least $400 for a luxe Chicago weekend getaway, you can book from over 60% off today!
Departure
- Charlotte
- Atlanta
- Fort Lauderdale
- New Orleans
- Phoenix
- Houston
- Orlando
- Los Angeles
- New York
- Las Vegas
- Denver
- Cincinnati
- Washington
Destination
- Chicago
Details
Here are some of the dates and departure airports we found for you, but there are many more available.
These fares are based on short layovers or nonstop journeys.
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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