Chicago Travel Deals

We have partnered with leading travel companies to bring you exclusive Chicago travel deals and savings. Save on top Chicago attractions and MORE with these great Chicago travel deals!

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Advertisement Chicago - $25 Gift Certificates for $10

  • Airfare, Hotels, Rental Cars, Vacation Packages

    Looking for a specific flight, hotel, rental car, or vacation package? No problem. Just tell us what you want and we'll search through thousands of published itineraries and prices. We'll instantly show you an easy-to-compare product and pricing chart drawn from the thousands of flights, hotels, rental cars and cruises available to priceline. Then, just choose what works for you. We do all the work so you can find exactly what you want in seconds. Start your next search from the priceline.com home page.

    Priceline.com Hotels - save up to 50%

  • Airport Shuttle

    Need a ride from Chicago O’Hare (ORD) or Midway (MDW) Airport? GO Airport Shuttle is the world’s largest airport shuttle company providing the most economical, convenient and safe way to get to and from the airport.

    Book an airport shuttle through the Smart Destinations Web Reservation Portal

  • Heading to Chicago? Before your trip, sign up with Groupon and save money! Groupon features a local daily deal on the best stuff to do, see, eat, and buy in Chicagoland. You’ll be able to save up to 90% on select offers.

    See today’s daily deal or sign up for Groupon Chicago

  • Top Destinations - Chicago

    Hotels.com offers more than 85,000 properties worldwide in over 400 destinations—including a wide selection in Chicago! From hotels and B&B's to condos and all inclusive resorts, Hotels.com knows the hotel experience is an important part of your trip! Hotels.com offers travelers the information they need to book the perfect trip all backed by the hotels.com Low Price Guarantee. Plus, Hotels.com specializes in providing travelers with accommodations during sold-out periods.

    Great Deals with Hotels.com

  • Restaurant.com connects restaurant seekers and food lovers to savings at more than 10,000 restaurants nationwide and to various online retailers. As the nationÕs leading online directory of restaurants and restaurant gift certificate provider, the company brings people together to relax, converse and enjoy well-prepared and -served meals at affordable prices.

    Save on Breakfast, Lunch and Dinner at Restaurant.com

Recommended Travel Guide Books To complement our free guide books our travel experts have recommended these additional guide books to give you a complete picture of the destinations we serve.

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Chicago Hotel Packages

We have partnered with leading travel companies to bring you exclusive deals on Chicago hotel packages. Save on Chicago hotel packages including UNLIMITED attraction admissions with the Go Chicago Card.

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Chicago's Essex Inn Chicago's Essex Inn
Chicago has so much to offer and the Essex Inn is within reach of just about anything your heart desires: world class theater, stunning art museums, winning sports teams, concerts, parks, local attractions and "magnificent" shopping. At the Essex Inn, you'll find comfort, personal service, an...

Get a great deal on an Essex Inn Go City Card Package

Hyatt Regency Chicago Hyatt Regency Chicago
Rising above the Chicago River, Hyatt Regency Chicago lays adjacent to the Chicago Loop business district and the Magnificent Mile shopping and dining areas. This breathtaking hotel features 2,018 guest rooms including 119 suites, 337 new Deluxe rooms, and an exclusive Regency Club.

Get a great deal on a Hyatt Go City Card Package

W Chicago Lakeshore W Chicago Lakeshore
Why not get a new perspective on things? Experience Chicago from an entirely different view, a refreshing water view to be exact. Situated along Lake Shore Drive near the Navy Pier, W Chicago Lakeshore is the only hotel in Chicago directly overlooking Lake Michigan and has received four Diamonds...

Get a great deal on a 'W' Go City Card Package

JW Marriott Chicago JW Marriott Chicago
Experience the best attractions Chicago has to offer by taking advantage of the Go Card All Access package from the JW Marriott Chicago. Enjoy access to the area's top attractions including the Field Museum, Shedd Aquarium, Shoreline Sightseeing Architectural River Cruise and Skydeck Chicago just to name a few....

Get a great deal on a JW Marriott Go City Card Package

Palmer House Palmer House
The Chicago Hotel the World Knows Best! At the Palmer House Hiltonhotel in Chicago, Illinois, guests enjoy the close proximity to the Art Institute of Chicago, Grant Park, Millennium Park and Navy Pier. State Street and Michigan Avenue shopping is just outside our hotel doors. Package includes standard room for two nights plus a 2-day Go Chicago Card for 2 adults.

Get a great deal on a Palmer House Go City Card Package.

Hilton Chicago Hilton Chicago
Hilton Chicago is a landmark downtown pet friendly property located on the "Cultural Michigan Avenue Mile" overlooking Grant Park and Lake Michigan, Millennium Park and Museum Campus. It is the closest luxury hotel to the city's convention center while being only minutes from the loop business. Package includes standard room for two nights plus a 2-day Go Chicago Card for 2 adults.

Get a great deal on a Hilton Go City Card Package.