Chicago Vacations from $419

Book a Hotel + Flight or Car together to unlock savings

Choose one or more items to build your trip:
    Plan, book, travel with confidence
  • payments icon
    Better together
    Save up to $580 when you book a flight and hotel together*
  • lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Your Chicago Vacation

The cultural experiences and cosmopolitan vibe are just the beginning of the things Chicago has on offer. Experience the very best of this interesting city your way with a customized Chicago vacation package. Ready to explore? Wrigley Field, Millennium Park and Willis Tower are just three of the leading places to visit during a trip to Chicago. Stop daydreaming and start traveling. Check out the multitude of options on Expedia today and put your Chicago vacation plans into motion!

The Latest Chicago Vacation Packages

Pendry Chicago
Congress Plaza Hotel
Swissotel - Chicago
Fairmont Chicago at Millennium Park Gold Experience
LondonHouse Chicago, Curio Collection by Hilton
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 Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
2,720,500
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Chicago Riverwalk, John G. Shedd Aquarium and Art Institute of 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 $125 per night from Apr 1 to Apr 2
$125
$147 total
includes taxes & fees
Apr 1 - Apr 2
7.6/10 Good! (6,459 reviews)
"As others have mentioned, this place is daaaaated. It was probably a fancy hotel back in its time but it definitely older now. That being said, it's a great place location wise particularly given the price. The rooms are old but clean. The service is good. The heating is centralized and it was cold ..."

Reviewed on Mar 28, 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 $119 per night from Apr 1 to Apr 2
$119
$140 total
includes taxes & fees
Apr 1 - Apr 2
8.6/10 Excellent! (2,720 reviews)
"ㆍ"

Reviewed on Mar 28, 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 $99 per night from Mar 31 to Apr 1
$99
$116 total
includes taxes & fees
Mar 31 - Apr 1
8.4/10 Very Good! (2,928 reviews)
"Good deal. Small room. Pretty small lobby. Comfortable bed and pillows. Staff was great. Location was amazing. Easy walk to any of the downtown theaters. Lots of restaurants close by. Would stay again!"

Reviewed on Mar 28, 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 $419, 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

Other vacations you might like

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