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3-Day Weekend Getaways From $380
Break down the Windy City into one convenient weekend package filled with the activities, hotels, and flights that suit you best. Whether you want shopping, cutting-edge art, or skyscraping views, below you’ll find some of our favorite Chicago neighborhoods. Choose one of these and dive into this deep dish of a city, or mix and match from hundreds of options to create your own perfect escape.Chicago Getaway Packages
Shopping and All That Jazz
- Neighborhood: Magnificent Mile
- More than Magnificent, this Mile of over 460 retail stores is not just for shoppers--there are enough jazz clubs, steak houses, and theatres to keep all ages wanting to twist and shout.
- Featured Hotels:
- The Sutton Place Hotel Chicago
- Flight, 3 Nights Hotel, Taxes & Fees
From $582 - Hard Rock Hotel Chicago
- Flight, 3 Nights Hotel, Taxes & Fees
From $439
Oh Baby, Don’t You Want to Go?
- Neighborhood: River North
- Go gaga for the highest number of art galleries outside of Manhattan, sink your teeth into a dreamy slice of deep-dish pizza pie, and hop from bar to bar listening to live local bands.
- Featured Hotels:
- Amalfi Hotel Chicago
- Flight, 3 Nights Hotel, Taxes & Fees
From $479 - Hotel Sax Chicago
- Flight, 3 Nights Hotel, Taxes & Fees
From $463
Sweet Home Chicago Skyscrapers
- Neighborhood: The Downtown Loop
- The Sears Tower has lots of company as it scrapes the sky in this storied district overlooking Lake Michigan, and it’s easy to see it all by taking the city’s famous “L” trains.
- Featured Hotels:
- Best Western Grant Park Hotel
- Flight, 3 Nights Hotel, Taxes & Fees
From $383 - Chicago's Essex Inn
- Flight, 3 Nights Hotel, Taxes & Fees
From $380
Prices are in USD for one adult based on double occupancy and include tax recovery charges. Sample prices gathered on 7/1607 for travel 8/26/07- 8/29/07 from Dallas (DFW). Our real-time dynamic Flight + Hotel packaging engine is constantly updating prices and availability. Please check pricing and availability for your travel dates and departure city on this site.