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
Chicago Getaway with Boutique Hotel 📣🔥
4-Night Chicago Vacation Starting from $283—Includes Nonstop Flights & Centric Hotel
From $283
Chicago might be in the cards for 2023! We've found fantastic prices on a 4-night getaway to the Windy City. It includes a stay at the 4-star Claridge House Hotel (4/5 on TripAdvisor & winner of the 2021 Travelers' Choice Award) and round-trip airfare from several US Cities, starting from $283 per person.
Departure
- Boston
- New York City
- Dallas
- Los Angeles
- Las Vegas
- Miami
- Orlando
Destination
- Chicago
Details
We found some of the dates with the best rates for you, but there are many other available.
All prices listed are based on nonstop journeys. You can click on the deal to see all the flight options and choose the more convenient for you.
Example of Cheapest Date
Additional Information
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*All of our deals are available at the time of publishing, but prices are subject to fluctuations and changes at any time.
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