Downtown Chicago Holidays

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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 hotels in Magnificent Mile

Top hotels in Downtown Chicago

Palmer House a Hilton Hotel
Palmer House a Hilton Hotel
4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$256 per night from 10 Jan to 11 Jan
S$256
includes taxes & fees
10 Jan - 11 Jan,2025
8.2/10 Very Good! (1,517 reviews)
"This was a perfect location to see the Christmas sites and to visit the stores on State Street."

Reviewed on 16 Dec,2024

Palmer House a Hilton Hotel
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 S$166 per night from 23 Dec to 24 Dec
S$166
includes taxes & fees
23 Dec - 24 Dec
7.8/10 Good! (8,256 reviews)
"For the price the property was great! The room we stayed in looked like it was recently done and was huge with nice beds and redone bathroom. You could tell the age of the building though. Many rooms on our floor were padlocked - perhaps just hadn't been refinished (hotel is huge so perhaps not all ..."

Reviewed on 19 Dec,2024

Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown River North
4 out of 5
600 N State St, Chicago, IL
The price is S$170 per night from 12 Jan to 13 Jan
S$170
includes taxes & fees
12 Jan - 13 Jan,2025
8.2/10 Very Good! (3,351 reviews)
"Everything was great. Hotel, happy hour Everyday. Complimentary breakfast. Wow!"

Reviewed on 19 Dec,2024

Embassy Suites by Hilton Chicago Downtown River North
See all 1,676 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 1,000,000 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 modern architecture, a city and autumn leaves

Millennium Park

4.5/5(147 reviews)

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park
Grant Park

Grant Park

4.5/5(96 reviews)

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park
Willis Tower featuring central business district, a city and interior views

Willis Tower

4.5/5(81 reviews)

The Skydeck at Willis Tower offers the best place in Chicago for a bird’s eye view across the breadth of the city and Lake Michigan.

Willis Tower

Things to do

Flyover in Chicago

Flyover in Chicago

S$51
per adult
94% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

S$65
per adult
94% of travellers recommend
Architecture River Tour
Color Factory Chicago Ticket

Color Factory Chicago Ticket

S$46
per adult
Color Factory Chicago Ticket
See all activities in Chicago

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.