Chicago Vacation Packages

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Your Chicago Vacation

From its cosmopolitan vibe to its cultural experiences and beyond, there's a whole lot to like about Chicago. Discover the wonders of this awesome city with a Chicago vacation package that's tailor-made for you. Make your trip to Chicago even more exciting by including some sightseeing. Wrigley Field, Millennium Park and Art Institute of Chicago are some of the major attractions worth exploring. Browse Expedia's wide range of travel options and book your ultimate vacation to Chicago now.

Top Chicago Vacation Deals

21c Museum Hotel Chicago
LondonHouse Chicago, Curio Collection by Hilton
JW Marriott Chicago
Fairmont Chicago at Millennium Park Gold Experience
Arlo Chicago
Prices and availability subject to change. Additional terms may apply.

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

Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $145 per night from Apr. 1 to Apr. 2
CA $145
CA $170 total
includes taxes & fees
Apr 1 - Apr 2
7.6/10 Good! (6,355 reviews)
"Stayed in a double and the room was absolutely massive. The building was built in the late 1800s, so the hallways are very wide and some guest rooms are huge like where they would have had a sitting room included back in the day. Everything was well maintained and the staff was super polite. Would ..."

Reviewed on Mar. 18, 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $140 per night from Mar. 31 to Apr. 1
CA $140
CA $165 total
includes taxes & fees
Mar 31 - Apr 1
8.6/10 Excellent! (2,655 reviews)
"Love it"

Reviewed on Mar. 17, 2024

River Hotel
Club Quarters Hotel, Central Loop, Chicago
Club Quarters Hotel, Central Loop, Chicago
4 out of 5
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $121 per night from Mar. 24 to Mar. 25
CA $121
CA $142 total
includes taxes & fees
Mar 24 - Mar 25
8.4/10 Very Good! (2,875 reviews)
Efficient Staff
"The staff and how things are run are very efficient! Friendly and helpful people working the desk. I found my stay to be very comfortable and the location was perfect to get around Chicago! They have a great system in place to store your luggage before and even checkout time if you need to venture ..."

Reviewed on Mar. 17, 2024

Club Quarters Hotel, Central Loop, 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.

Explore other types of vacation packages

Frequently asked questions

How much does a Chicago vacation package cost?
Starting from as low as CA $662, you can handcraft your own Chicago package the way you want. Simply bundle hotels, flights and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Chicago?
Find flights that fit in with your schedule, add a hotel to your booking and watch how much you save with a Chicago vacation package. It’s as easy as that! From flights and hotels to activities and rental cars, Expedia is where your cheap getaway begins. And with more than 550 partner airlines and 1,000,000 properties across the globe to pick from, you won’t be short of choice.
Where should I stay in Chicago?
Central Chicago is an excellent place to stay in Chicago. With interesting attractions like Millennium Park and Willis Tower within easy reach, you won’t have to worry about running out of things to do here. Magnificent Mile is another option. This place has plenty to offer travelers, including John Hancock Center and Chicago Water Tower.
What are the top hotels in Chicago?
Congress Plaza Hotel and LondonHouse Chicago, Curio Collection by Hilton are some favorite options in the neighborhood of Central Chicago. If you’d rather stay in the North Side area, consider locking in a room at The Whitehall Hotel or Hyatt Regency Chicago.
How far in advance should I book my Chicago vacation?
While not all air carriers release ticket prices early, you can normally start comparing international flights on Expedia up to 12 months in advance. This is the time you can bag some fantastic deals. If you’re booking last minute, you may still be in luck. Discounted prices occasionally appear a few weeks prior to departure.
What does an Expedia Chicago travel package include?
Hotels, flights and rental cars — we have them well covered. With Expedia, you can shape your Chicago package just how you like it. All you have to do is work out exactly what you need. Once you’ve made your booking, you can add on fun things like tours and activities. The more you bundle, the greater your savings!
What should I know before booking a Chicago travel package?
We already have low prices. However, you’ll pick up even more bargains when you book your flights, hotels and car rentals together. With an Expedia travel package, you’ll always get transparent pricing and a huge range of choice.
Can I choose my airline with a Chicago Expedia vacation package?
Yes, of course. We have more than 550 partner airlines globally, so fly with the carrier that fits your budget and travel needs.
If I'm not able to travel, can I cancel my Chicago vacation package?
We totally get that life sometimes gets in the way of your plans. If you’ve booked a Chicago vacation package and have to amend or cancel it, we’re here to help. We suggest visiting our Customer Service Portal first for information. But generally speaking, if you’ve booked your package in the last 24 hours, you may be able to cancel or change your itinerary at no cost. If it’s been longer than 24 hours, your airline, hotel or car rental company may charge a fee.

Discover the most popular places to visit in Chicago

What to do in Chicago

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.