Search over 1 million properties and 550 airlines worldwide
Free cancellation on most hotels. Because flexibility matters.
Most Chicago hotels offer free cancellation. Consider booking refundable hotels rather than non-refundable ones. Just look for the ‘free cancellation’ message during your hotel search. Prices can vary, but right now we believe that flexibility matters.
For more information about the impact of COVID-19 on your Chicago trip, please visit our Coronavirus Information page (opens in new window).
Yes! Get instant savings by booking a Chicago vacation package. Just pick your favorite options and let Expedia take care of the rest.
If you book a package deal on Expedia, you can save as much as $583*.
Look around our universal database of more than 550 airline partners and 1,000,000 properties worldwide. Too many to select from? Don't worry — we'll help you decide!
If you change your plans, we will honor your cancellation request on almost all bookings with no extra fee.
Preparing for your trip to Chicago? Need some info about what to see when you arrive? That's where we can assist!
Take it from us, your bucket list will be heaps shorter after a trip to Chicago! Famed attractions like the Art Institute of Chicago and Willis Tower should be some of your first ports of call. The McCormick Place and the University of Illinois Chicago also draw in crowds of travelers from all across the globe.
You're going to find yourself surrounded by terrific things to do and see, including Navy Pier and the Lincoln Park Zoo. If you're dying to get the most out of your stay, also check out Lincoln Park and the Chicago Cultural Center.
Millennium Park is an oasis amid the bustle of everyday life. Pull off your shoes and feel the cool grass beneath your feet or simply lie on your back and spot shapes in the clouds. Adventurers in this destination have heaps of options. Those who are a little queasy around heights might want to look away, but anyone who's curious about skyscrapers can't miss John Hancock Center. Towering high above the ground, it's a beloved fixture of the area's skyline. Still have some time on your hands? Want to catch a sunrise among some spectacular scenery? Skydeck Ledge boasts glorious views that deserve to be photographed.
When we hark back to our travels, we usually remember experiences rather than our swish hotel room and its view of the pool. Are you ready to create some new travel memories?
Your trip to Chicago is about to get a lot more exciting. There are heaps of activities available, such as:
To check out all the activities on offer, head to our Chicago things to do page.
With no less than 165 accommodations in Chicago, finding a place to stay won't be difficult. But why wait around? Book now via Expedia and kick-start your next cheap vacation or luxury getaway.
Begin the quest for a dreamy Chicago base by looking into the latest offers at the Chicago Premier Suites (540 N State Street) and The Peninsula Chicago (108 East Superior Street). Alternatively, the Trump International Hotel & Tower Chicago (401 N Wabash Ave) and the Old Chicago Inn (3222 N Sheffield Ave) are two properties well worth investigating if you're traveling on the cheap.
We know the airport won't be the most memorable moment of your vacation, but there's nothing like the excitement of knowing that your well-deserved trip to Chicago is just a flight away! Once you unbuckle your seatbelt at Midway International Airport (MDW), you'll be 9 miles from the heart of town.
*Savings based on all vacation package bookings with Flight + Hotel on Expedia.com from January through December 2020, as compared to price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.
What are the advantages of a road trip to Chicago?
There’s nothing quite like a Chicago road trip. And Expedia makes it easy for you to turn all those road trip ideas into reality. You can find cheap deals on hotels in Chicago or bundle your hotels with car rentals to save even more. With our Chicago packages, you’ll find hitting the highway for that road trip adventure is more affordable than ever.
How to plan a road trip to Chicago?
Planning a road trip can feel daunting, especially when you’ll be making multiple bookings for your itinerary. But you can find car rentals and low rates on hotels all in one place— Expedia. How you plan your road trip depends on what’s important to you. People love to take road trips to experience the great outdoors, bond with friends or family and see more of the world. When planning, bundle your car rental and hotel into one discounted package to maximize savings on both. Or, leave room for spontaneity, booking what you need when you need it with our last-minute deals.
What to do on a road trip to Chicago?
When taking a road trip adventure, it’s best to plan how you want to spend your time on your road trip itinerary. We don’t want you to miss out on any of the best things to do in Chicago. You can book all the road trip activities on your Chicago wishlist, and even plan activities along your route as well.
How to rent a car for a road trip to Chicago?
For an epic road trip, you'll need the perfect car. Renting a car for a road trip is the best option that doesn’t put miles or strain on your vehicle, and especially when it's also so affordable. Because when you book on Expedia, it doesn't need to be expensive. You can pick up a cheap car rental and head out to one of these incredible vacation rentals in Chicago. And when you bundle car rentals with hotel stays, you'll save even more on each part of your journey.
Really enjoyed my stay at London House.... I have not one complaint!!
The staff is always nice and helpful. The rooms are always clean! I normally enjoy my stay when I’m here! Great property!
Great place to be I love it there only hotel I go
Nice room , And the staff was very friendly I will stay here again
Great hotel. Very accommodating during Covid and the riots downtown.