Real deals


Search by

Cities
Leaving From

You're searching for 'Chicago'.
Displaying 1 – 9 of 9 Real Deals currently available.

Hotel Deals in Chicago

From $89

Trivago

Save up to 35% on your next Hotel! Book Now and Save!

Chicago: 4-Star Starwood Hotel Summer Sale

From $189

Must book by May 31, 2016, 11:59 PM

Starwood Hotels & Resorts

Chicago to New Orleans, Mississippi River Cruise, Luxury Train, 9 Nights

From $2,995

Exposurestonature/Dreamstime

Call this the ultimate American adventure. Travel by train along the Mississippi River with this incredible travel package from Uncommon Journeys.

Must book by Nov. 26, 2016, 11:00 PM

Fall Fare Sale to/from Las Vegas, O/W

From $69

Must book by June 30, 2016, 11:59 PM

Virgin America

Hotel Deals in Chicago (Metropolitan Area)

From $49

Trivago

We know everything about Hotels. Find your ideal Hotel on trivago.com

Seattle Fares on Award-Winning Airline, O/W

From $98

Must book by June 30, 2016, 11:59 PM

Virgin America

San Francisco from San Diego, One Way

From $109

Must book by June 30, 2016, 11:59 PM

Virgin America

Nationwide Fare Sale from San Francisco, O/W

From $89

Must book by June 30, 2016, 11:59 PM

Virgin America

Nationwide Fare Sale from Los Angeles, O/W

From $69

Must book by June 30, 2016, 11:59 PM

Virgin America

Our newsletter delivers vacation inspiration straight to your inbox.

Check Prices