Clearing Holidays

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    • Better together

    Save up to S$134 when you book a flight and hotel together*

    Find the right fit

    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$259 per night from 2 Nov to 3 Nov
S$259
2 Nov - 3 Nov
includes taxes & fees
7.8/10 Good! (9,576 reviews)
All good.

Reviewed on 25 Oct, 2025

Congress Plaza Hotel
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
350 West Wolf Point Plaza, Building 2, Chicago, IL
Fully refundable
The price is S$183 per night from 24 Nov to 25 Nov
S$183
24 Nov - 25 Nov
includes taxes & fees
8.8/10 Excellent! (1,958 reviews)
The room was very nice and clean. The bed was really comfortable. Staff was very helpful and the restaurant was excellent. Definitely would stay here again.

Reviewed on 20 Oct, 2025

Holiday Inn Chicago Dwtn - The Mart by IHG
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$167 per night from 16 Nov to 17 Nov
S$167
16 Nov - 17 Nov
includes taxes & fees
8.8/10 Excellent! (3,138 reviews)
Clean room, great staff, perfect location.

Reviewed on 23 Oct, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,821 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$63
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

S$57
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

S$138
per adult
84% of travellers recommend
Chicago C3® by CityPASS®
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.