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Luxe Chicago Weekend Trip from $139 Including an Award-Winning Hilton Hotel & Flights!
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!
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.