Downtown Chicago Holidays

Book a Hotel + Flight or Car together to unlock savings

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
Magnificent Mile - River North

Magnificent Mile

Are you interested in fascinating museums, panoramic lake views and popular shops? A visit to Magnificent Mile might be the perfect thing. You can also explore top sights like Michigan Avenue and Chicago Water Tower.

Find hotel + flight trips in Magnificent Mile

Top hotels in Downtown 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 2.657.502 ₫ per night from 23 Dec to 24 Dec
2.657.502 ₫
3.119.642 ₫ total
includes taxes & fees
23 Dec - 24 Dec
7.8/10 Good! (7,955 reviews)
"Wallpaper in lobby is old. No working ice machines to be found."

Reviewed on 21 Dec 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 2.367.315 ₫ per night from 21 Jan to 22 Jan
2.367.315 ₫
2.778.992 ₫ total
includes taxes & fees
21 Jan - 22 Jan 2025
8.6/10 Excellent! (3,626 reviews)
"Having to park my car 4 blocks away"

Reviewed on 22 Dec 2024

River Hotel
Hyatt Regency Chicago
Hyatt Regency Chicago
4 out of 5
151 East Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is 3.757.158 ₫ per night from 5 Jan to 6 Jan
3.757.158 ₫
5.157.633 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2025
9/10 Wonderful! (3,125 reviews)
"We were upgraded to a room with a view of the river wh"

Reviewed on 22 Dec 2024

Hyatt Regency Chicago
See all 1,675 properties in Downtown 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 Downtown Chicago holiday package cost?
Go from looking to booking with our Downtown Chicago holiday packages, which start from just . 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 1null000null000 hotels across the world, your Downtown Chicago holiday 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 holiday you’ve always dreamed of in Downtown Chicago is much closer than you thought!
How far in advance should I book my Downtown Chicago holiday?
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 holiday package?
Yes — that’s the beauty of an Expedia holiday 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 holiday 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 holiday 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.

Popular places to visit

Millennium Park which includes autumn colours, modern architecture and street scenes

Millennium Park

4.5/5(147 reviews)

Explore the great outdoors with a trip to Millennium Park, a popular green space in Chicago. Stroll along the riverfront or visit the notable monuments in this vibrant area.

Millennium Park
Grant Park

Grant Park

4.5/5(96 reviews)

Explore the great outdoors with a trip to Grant Park, a popular green space in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

Grant Park
Willis Tower which includes a high-rise building, views and interior views

Willis Tower

4.5/5(81 reviews)

Learn about the local history of Chicago when you take a trip to Willis Tower. Discover the entertainment choices and notable monuments in this vibrant area.

Willis Tower