Clearing Vacations from $348

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Your Clearing Vacation

Your next big journey is calling your name with a vacation package to Clearing. Entertainment, relaxation and nonstop great times — you're sure to find it in this neighborhood. Your trip to Clearing wouldn't be complete without a visit to big-name attractions nearby such as SeatGeek Stadium, Morton College and Hawthorne Works Museum. Whatever your dream Clearing vacation looks like, you can make it a reality with Expedia.

The Latest Clearing Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago/Oak Lawn

Hilton Chicago/Oak Lawn

3.5 out of 5
Save 100% on your flight
Price was $608, price is now $348 per person
$348
per person
Dec 25 - Dec 30
found 10 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.2/10 Very Good! (1,020 reviews)
We just spent 2 nights it was clean, nice would stay here again, didnt have time to use the pool or fitness room. The only thing i missed was a microwave.

Reviewed on Oct 16, 2025

Art Villa

Art Villa

5 out of 5
West Town
Save 100% on your flight
Price was $1,371, price is now $741 per person
$741
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
10/10 Exceptional! (2 reviews)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,293, price is now $728 per person
$728
per person
Nov 25 - Dec 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
Staff friendly and convenient. However, a bit loud, like we were on the sidewalk hearing music, cars and trains. Room was very minimal and a bit stark. Most like a dorm room/hostel. Very low lighting, fine except to try to read at night.

Reviewed on Oct 15, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,123, price is now $659 per person
$659
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Excellent luxury atmosphere with second to none customer service. The bathroom was very nice. Although the toilet has a slight odor that was unexpected for the high quality room and hotel.

Reviewed on Oct 15, 2025

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,306, price is now $788 per person
$788
per person
Dec 31 - Jan 3
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
This is a very nice hotel. The staff is super accommodating. The location is one of the best in the area for shopping and dining.

Reviewed on Oct 14, 2025

Where to stay in Clearing

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

Clearing Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $170 total per night from Nov 2 to Nov 3
$170 total
Nov 2 - Nov 3
Total with taxes and fees
7.8/10 Good! (9,439 reviews)
Pleasant Stay for business
"Great location for downtown walking. The bar staff was friendly. I was here on business. The desk area didn't have any electrical outlets nearby for working but I get this isn't strictly a business hotel. If I was on vacation in CHI, this place would be ideal. Great value and the location was perfect. ..."

Reviewed on Oct 16, 2025

Congress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $109 total per night from Nov 10 to Nov 11
$109 total
Nov 10 - Nov 11
Total with taxes and fees
7.8/10 Good! (2,480 reviews)
"I was there for the marathon and had a shared female room — the three others ended up being runners too, which was great. The location is fun and lively, but my room on the 9th floor was quiet. The staff were really nice — one of them even lent me his luck for the locker and gave me a card for the ..."

Reviewed on Oct 16, 2025

Freehand Chicago
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
$112 nightly
The price is $132 total per night from Nov 16 to Nov 17
$132 total
Nov 16 - Nov 17
Total with taxes and fees
8.8/10 Excellent! (3,118 reviews)
"Clean, quiet, safe!"

Reviewed on Oct 15, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,822 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.
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All Inclusive Vacations
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Kid Friendly Vacations

Discover the most popular places to visit in Clearing

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

4.5/5(332 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

River tour boat in Chicago

Architecture River Tour

$49
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

$44
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel 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.