A Haven for the Hip-at-Heart
Experience Chicago From $333

Calling all art lovers, foodies, and shopaholics! If you haven’t visited Chicago yet, you’re missing out. With cutting-edge architecture, compelling museums, vibrant nightlife, and a smorgasbord of top-notch restaurants and boutiques, the Windy City is a haven for discerning travelers. With these deals on Chicago vacations, you’ll have more dough left to live it up in this fascinating city.

Flight + Hotel getaways start at just $333. Book your Chicago vacation today.

The Peninsula Hotel Chicago Flight + 4 Night Hotel from $880 Nightly Rates From $ Great Winter Rates	Four Points by Sheraton Chicago Magnificent Mile Flight + 4 Night Hotel from $376 Nightly Rates From $ Save 15%
W Chicago - City Center Flight + 4 Night Hotel from $440 Nightly Rates From $ Save up to 20%	The Dana Hotel Chicago Flight + 4 Night Hotel from $511 Nightly Rates From $ Stay 2 Nights and Save 15%
Hard Rock Hotel Chicago Flight + 4 Night Hotel from $451 Nightly Rates From $ Save up to 30%	The Ambassador East Hotel Flight + 4 Night Hotel from $348 Nightly Rates From $ Save up to 30%
Tremont Hotel Flight + 4 Night Hotel from $333 Nightly Rates From $ Save up to 25%	The Silversmith Hotel Chicago Flight + 4 Night Hotel from $393 Nightly Rates From $ Save up to 30%
The Sutton Place Hotel Chicago Flight + 4 Night Hotel from $447 Nightly Rates From $ Great Winter Rates	Travelodge Chicago Flight + 4 Night Hotel from $455 Nightly Rates From $ Stay 2 Nights and Save 20%

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Terms & Conditions

*The 15% - 30% off offers apply only at participating hotels. Discount is based on length of stay and will be subtracted from the price of the hotel or the hotel component of any Flight + Hotel vacation package. The discount is based upon the total hotel price excluding taxes and other fees. Offers vary by hotel, are subject to availability, and may be discontinued without notice. Additional restrictions and blackout dates may apply.

**Prices are in USD for one adult based on double occupancy and include tax recovery charges. Sample prices were found recently by Travelocity or its customers for travel 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.