Downtown Chicago Vacations from ¥372,066

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The Latest Downtown Chicago Vacation Packages

Trump International Hotel & Tower Chicago
LondonHouse Chicago, Curio Collection by Hilton
Level Chicago – Old Town
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
Pendry Chicago
Prices and availability subject to change. Additional terms may apply.

Where to stay in Downtown Chicago

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

Downtown 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 ¥14,241 per night from Mar 31 to Apr 1
¥14,241
per night
Mar 31 - Apr 1
8.4/10 Very Good! (2,931 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
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 ¥16,838 per night from Apr 1 to Apr 2
¥16,838
per night
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 ¥15,680 per night from Mar 31 to Apr 1
¥15,680
per night
Mar 31 - Apr 1
8.6/10 Excellent! (2,720 reviews)
"ㆍ"

Reviewed on Mar 28, 2024

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 Downtown Chicago vacation package cost?
Go from looking to booking with our Downtown Chicago vacation packages, which start from just ¥372,066. Handpick the hotels and flights that suit your travel style. Then, add on a couple of tours or activities for an amazing adventure.
How do I get a cheap travel package to Downtown Chicago?
Bundle your bookings with Expedia to save big on your next trip. With more than 550 partner airlines and 1,000,000 hotels across the world, your Downtown Chicago vacation package can be tailored exactly to suit your budget. With all that extra money, why not include one or two fun tours and activities? It’s an easy way to unlock even more savings. The vacation you’ve always dreamed of in Downtown Chicago is much closer than you thought!
How far in advance should I book my Downtown Chicago vacation?
While not all airlines advertise tickets early, you can normally look up international airfares on Expedia up to 12 months in advance. This is the time you’ll score some incredible deals. If you’ve left things to the last minute, you could still be in luck. Discounted prices occasionally emerge a few weeks before departure.
What does an Expedia Downtown Chicago travel package include?
Packages include flights, hotels and rental cars, but you can mix and match them to create your ideal Downtown Chicago trip. You can also add on fun things like activities and tours once you’ve made your booking. You’re in charge! When you combine your bookings with Expedia, you’ll score discounts you won’t find elsewhere.
What should I know before booking a Downtown Chicago travel package?
Our prices are always low. However, you’ll pick up even better deals if you book your hotels, flights and car rentals together. With an Expedia travel package, you’ll get transparent pricing and tons of choice.
Can I choose my airline with a Downtown Chicago Expedia vacation package?
Yes — that’s the beauty of an Expedia vacation package. You’re in charge! We have more than 550 partner airlines throughout the world, so you have lots of choice when arranging your Downtown Chicago trip.
If I'm not able to travel, can I cancel my Downtown Chicago vacation package?
You can. We understand that even the best-laid plans can go awry, so we’re happy to help if you have to make changes to your Downtown Chicago vacation package. You may be able to change or cancel your itinerary for free if you’ve booked in the last 24 hours. Your airline, hotel or car rental company may impose a fee if your booking was made more than 24 hours ago. Have a look at our Customer Service Portal for further information. Also, be sure to check your itinerary for the finer details on change fees.

Discover the most popular places to visit in Downtown Chicago

Things to do

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