A Haven for the Hip-at-Heart

Experience Chicago From $89

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 $345. Book your Chicago stay today.

Featured Hotels
	The Allerton Hotel Chicago Great Fall Rates Nightly Rates From $ Flight + 4 Nights From $434
	Omni Chicago Hotel Book Now and Save Nightly Rates From $ Flight + 4 Nights From $568
	The Ritz Carlton Chicago Great Fall Savings Nightly Rates From $ Flight + 4 Nights From $707
	The Peninsula Hotel Get the 3rd Night Free Nightly Rates From $ Flight + 4 Nights From $1,013
	The Avenue Hotel Chicago Save 25% Nightly Rates From $ Flight + 4 Nights From $475
	W Lakeshore $50 Amex Gift card, Free Parking, Breakfast, and Upgrade Nightly Rates From $ Flight + 4 Nights From $444
	W Chicago City Center Save 50% on Parking, Get a Free Breakfast Nightly Rates From $ Flight + 4 Nights From $397
	Sheraton Chicago Hotel & Towers $100 Macy's Gift Card Nightly Rates From $ Flight + 4 Nights From $345
	Hotel 71 Save 15% on 2 Night Stay Plus Free Upgrade Nightly Rates From $ Flight + 4 Nights From $429
	Westin Michigan Avenue Save 10% Plus Free Parking Nightly Rates From $ Flight + 4 Nights From $408

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Activities

Chicago
The Field Museum - $22

Chicago
Progressive Dining Tour - $89

Chicago
Hancock Observatory - $15

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Terms and Conditions
*The 10% - 50% 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.