Chicago Vacations

Book a Hotel + Flight or Car together to unlock savings

    Plan, book, travel with confidence

  • payments icon
    Better together
    Save up to NT$5,755 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

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

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 NT$2,975 per night from Mar 21 to Mar 22
NT$2,975
per night
Mar 21 - Mar 22
8.4/10 Very Good! (2,873 reviews)
"Good value in downtown Chicago. Older building but updated well. Good coffee in room. Friendly staff. Validated parking. Would definitely stay again."

Reviewed on 2024/3/16

Club Quarters Hotel, Central Loop, Chicago
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 NT$3,397 per night from Apr 1 to Apr 2
NT$3,397
per night
Apr 1 - Apr 2
7.6/10 Good! (6,339 reviews)
"Nice location. Historic building with charm, but not shiny and new. Bed was extremely comfortable but my room faced the L so it was rather noisy. Maintenance being done on elevators on a busy friday night was inconvenient."

Reviewed on 2024/3/16

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 NT$3,275 per night from Mar 24 to Mar 25
NT$3,275
per night
Mar 24 - Mar 25
8.6/10 Excellent! (2,655 reviews)
"Love it"

Reviewed on 2024/3/17

River 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.

Frequently asked questions

How much does a Chicago vacation package cost?
Starting from as low as , 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

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