COVID-19 alert: Travel requirements are changing rapidly, including need for pre-travel COVID-19 testing and quarantine on arrival.

Chicago, IL Vacation Packages

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Chicago Vacation: Coronavirus Information

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).

Top Chicago Flight + Hotel Deals

The Langham, Chicago
Residence Inn Chicago Downtown/Loop
Swissotel - Chicago
DoubleTree by Hilton Chicago Midway Airport
The Westin Chicago River North

Where to stay in Chicago

Find the best Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Chicago

Top Hotels in Chicago

River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Free CancellationReserve now, pay when you stay
The price is $109 per night from May 16 to May 16
4.2/5Excellent! (2,365 reviews)
"Close to shopping, restaurants and movies"

Reviewed on May 8, 2021

River Hotel
The Whitehall Hotel
The Whitehall Hotel
4 out of 5
105 E Delaware Pl, Chicago, IL
Free CancellationReserve now, pay when you stay
The price is $74 per night from May 11 to May 11
4/5Very Good! (3,041 reviews)
"Perfect for a couple escape days n the Chicago city."

Reviewed on May 5, 2021

The Whitehall Hotel
Loews Chicago Hotel
Loews Chicago Hotel
4.5 out of 5
455 North Park Drive, Chicago, IL
Free CancellationReserve now, pay when you stay
The price is $169 per night from May 11 to May 11
4.7/5Exceptional! (1,369 reviews)
"Very beautiful and clean hotel, I highly recommend this hotel"

Reviewed on May 8, 2021

Loews Chicago Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top things to do in Chicago

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 in Chicago 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?

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.

Frequently asked questions

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