Clearing Holidays

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    Save up to S$134 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Where to stay in Clearing

Find the best Clearing areas and neighborhoods for the activities you enjoy most. Learn more about Clearing
Downtown Chicago which includes a city

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Top hotels in Clearing

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$283 per night from 14 Sept to 15 Sept
S$283
14 Sept - 15 Sept
includes taxes & fees
7.8/10 Good! (8,965 reviews)
"Its location is the main reason why I chose to stay. The room has been updated; it is roomy and clean. Staffs are very friendly and helpful."

Reviewed on 17 Aug, 2025

Congress Plaza Hotel
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$227 per night from 1 Sept to 2 Sept
S$227
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,187 reviews)
"Everything was great. Thanks for an awesome experience."

Reviewed on 15 Aug, 2025

The Wade
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$242 per night from 24 Aug to 25 Aug
S$242
24 Aug - 25 Aug
includes taxes & fees
8.4/10 Very Good! (4,708 reviews)
"The Italian restaurant inside is delicious, we went twice! If you aren’t I. The mood for there are so many options that are walkable. The Taco spot around the corner is also a win for food Taco Maya. The only thing we didn’t like is having to wait so long for the elevator, 25 mins to get from the ..."

Reviewed on 15 Aug, 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,910 properties in Clearing
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 Clearing holiday package cost?
Handcraft your Clearing holiday package from an affordable . Pick from any combination of hotels, flights and rental cars to put together the escape you've been dreaming about for ages. Remember to add on one or two experiences!
How do I get a cheap travel package to Clearing?
Bundle your flights and hotels with Expedia to save big on your next getaway. With more than 550 air carriers and 1,000,000 properties globally, your Clearing holiday package can be customized exactly to suit your budget. With all those extra dollars, why not throw in one or more fun experiences and tours? It's an easy way to unlock even more bargains. The holiday you've always dreamed of in Clearing is closer than you thought!
What are the top hotels in Clearing?
Whether you're staying for one or several nights in Clearing, you'll get a wonderful night's rest at Chicago Marriott Midway. This place is popular with lots of travellers.
How far in advance should I book my Clearing holiday?
Reserving your flight early with Expedia means one less thing to have to worry about. Many air carriers display prices up to 12 months prior to take off. Typically, this is the cheapest time to book. If circumstances have left you booking late, last-minute deals to Clearing sometimes occur in the weeks leading up to departure.
What does an Expedia Clearing travel package include?
Hotels, rental cars and flights, or any combination of them — it's up to you! Whether you're exploring Clearing with the entire family or enjoying a solo break, there's a package to match every style and budget. Once you've made your booking, why not add on a few tours and experiences?
What should I know before booking a Clearing travel package?
Our prices are already low. However, you'll enjoy even better deals if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and lots of choice.
Can I choose my airline with a Clearing Expedia holiday package?
Expedia offers access to more than 550 airline partners worldwide, so you sure can! Just select the airline you want and create your ideal Clearing escape.
If I'm not able to travel, can I cancel my Clearing holiday package?
If your travel plans in Clearing have changed, it's good to know that it is possible to cancel or amend your booking. If you booked in the last 24 hours, you may be eligible for a refund. If your booking was made more than 24 hours ago, your hotel, airline or car rental company may impose a fee. For more details, visit our Customer Service Portal.

Popular places to visit

Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
McCormick Place

McCormick Place

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Millennium Park which includes modern architecture, a city and autumn leaves

Millennium Park

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

Millennium Park

Things to do

River tour boat in Chicago

Architecture River Tour

S$53
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

S$58
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

S$52
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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.