Vacation to Chicago

Book a Hotel + Flight or Car together to unlock savings

Choose one or more items to build your trip:

Save up to 30% when you add a hotel to your flight as an Expedia member

Enjoy flexibility with our Book now Pay later option & fully refundable rates on most hotels

Customize your vacation with ease all in one place

Chicago Flight and Hotel Deals

Hotel Saint Clair- Magnificent Mile
21c Museum Hotel Chicago
The Langham, Chicago
Trump International Hotel & Tower Chicago
Chicago Athletic Association, a Hyatt Hotel

Chicago Essential Information

Prepare for your Chicago vacation with our essential travel info

Where to stay in Chicago

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

Chicago Hotel Deals

Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL, 60611
Fully refundableReserve now, pay when you stay
The price is $122 per night from May 30 to May 31
$122
per night
May 30 - May 31
7.2/10 Good! (1,389 reviews)
"The wait for the bellman to drop off and pick up was too long as no one was there for long periods"

Reviewed on May 23, 2023

Warwick Allerton - Chicago
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL, 60605
Fully refundableReserve now, pay when you stay
The price is $135 per night from May 30 to May 31
$135
per night
May 30 - May 31
7.4/10 Good! (4,176 reviews)
"👍"

Reviewed on May 28, 2023

Congress Plaza Hotel
Hyatt Regency Chicago
Hyatt Regency Chicago
4 out of 5
151 East Wacker Dr, Chicago, IL, 60601
Fully refundable
The price is $254 per night from Jun 18 to Jun 19
$254
per night
Jun 18 - Jun 19
8.6/10 Excellent! (2,570 reviews)
"I love this hotel! It was convenient and near all the local attractions. My room had a awesome view.The staff was very nice and professional. Room service was also excellent. Room very clean and that’s thing I look for when traveling. I would definitely stay here again and I highly recommend this ..."

Reviewed on May 28, 2023

Hyatt Regency Chicago
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.

Frequently asked questions

How much does a Chicago vacation package cost?
From as low as $235. Yes, you read that right. Our Chicago vacation packages are a great way to make your budget go further. Bundle your hotels, flights and rental car and get out and explore this fabulous destination.
If I'm not able to travel, can I cancel my Chicago vacation package?
If your vacation plans in Chicago have been upended, it’s a relief to know that it is possible to cancel or amend your booking. If you made your booking less than 24 hours ago, you may be able to get a refund. If your booking was made more than 24 hours ago, your hotel, airline or car rental company may impose fees. For more details, visit our Customer Service Portal.
How do I get a cheap travel package to Chicago?
Combine your hotel and flight bookings, toss in extras such as activities or a rental car, and save with a Chicago vacation package. You won’t just walk away with exciting discounts on your getaway — you’ll have loads of choice within your reach too. When you book with Expedia, you’ll have your pick of over 550 airlines and 1,000,000 hotels around the world. Your next big adventure begins right here, right now!
Where should I stay in Chicago?
If you’re eager to discover what makes Chicago tick, Near North Side is a terrific place to begin. From here, you’ll easily be able to access Navy Pier and Chicago Childrens Museum. Another neighborhood to consider is The Loop. Famed for Millennium Park and Willis Tower, it’s easy to see why many visitors end up here.
What are the top hotels in Chicago?
If you’re planning to stay in the Central Chicago neighborhood, some great options are Hyatt Regency Chicago and The Godfrey Hotel Chicago. North Side is also a favorite Chicago area. We recommend Hyatt Regency Chicago or The Godfrey Hotel Chicago if you prefer this part of town.
How far in advance should I book my Chicago vacation?
While not all air carriers release ticket prices early, you can normally look up international airfares on Expedia up to a year in advance. This is the time you’ll bag some incredible bargains. If you’re booking at the last minute, there’s a chance you could get lucky. Sometimes the lowest prices emerge only weeks before departure.
What does an Expedia Chicago travel package include?
From flights and hotels to rental cars, Expedia can help you shape a Chicago package that’s right for you. Heading away for a while? Check out a rental car, hotel and flight bundle. If you can only squeeze in a quick getaway, a hotel and flight deal could be more your style. Tours and activities can be added after you’ve booked. Our packages make it easy to save and plan.
What should I know before booking a Chicago travel package?
Our prices are always low. However, you’ll snap up even more bargains if you book your hotels, flights and car rentals together. With an Expedia package, you’ll always get transparent pricing and loads of choice.
Can I choose my airline with a Chicago Expedia vacation package?
Yes — that’s the beauty of an Expedia package. You’re in control. We have more than 550 airline partners globally, so you have loads of choice when planning your Chicago getaway.
Does Expedia offer Book Now, Pay Later Chicago vacation packages?
Having joined forces with online lender Affirm, Expedia provides financial freedom with a Book Now, Pay Later option for flight and hotel packages. Get the financial side of things out of the way with just one upfront payment or spread the cost of your package over a number of installments. It’s up to you.

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