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Jul 15 - Jul 16
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Jul 16 - Jul 17
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Jul 18 - Jul 20
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Compare 4,909 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

The Chicago Hotel Collection Ambassador Gold Coast
Enjoy a romantic breakfast on the balcony with a city view, surrounded by a selection of cheeses, fresh fruits, and nuts.

The Chicago Hotel Collection Ambassador Gold Coast

4.0 star property
8.2 out of 10, Very Good, (1030)
"Property was nice and a great location. Breakfast was good/convenient"
The price is ₩51,170
₩254,789 total
includes taxes & fees
Jul 27 - Jul 28
The Chicago Hotel Collection Ambassador Gold Coast
Claridge House
Experience the hotel's elegant lobby, featuring a reception area, comfortable seating, and a unique rug with the hotel's logo.

Claridge House

4.0 star property
8.8 out of 10, Excellent, (1259)
"Comfy bed and linens, nice amenities and the staff checked on me via text throughout the stay. "
The price is ₩146,095
₩212,092 total
includes taxes & fees
Jul 27 - Jul 28
Claridge House
Sable at Navy Pier Chicago, Curio Collection by Hilton
Relax in style with lounge chairs and bar stools amidst a scenic backdrop.

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
9.4 out of 10, Exceptional, (2067)
"Amazing property clean comfy bedding and wonderful views"
The price is ₩328,080
₩425,240 total
includes taxes & fees
Aug 7 - Aug 8
Sable at Navy Pier Chicago, Curio Collection by Hilton
Rainbow Motel
Relax in a serene bedroom with a large bed, minimalist decor, and a cityscape painting above.

Rainbow Motel

7.6 out of 10, Good, (4)
"It was a good stay the rooms are small tho but if you are going to have fun and just have somewhere to sleep then it’s perfect for a couple people "
The price is ₩123,706
₩145,219 total
includes taxes & fees
Jul 16 - Jul 17
Rainbow Motel
Carlton Inn Midway
Enjoy a self-service breakfast with a variety of options at this well-equipped breakfast bar.

Carlton Inn Midway

2.0 star property
6.6 out of 10, (1007)
"The female clerk was very friendly and helpful!"
The price is ₩144,823
₩170,007 total
includes taxes & fees
Jul 29 - Jul 30
Carlton Inn Midway
Skylark Motel
Skylark Motel's exterior features a prominent sign with its name displayed in bold letters.

Skylark Motel

2.0 star property
4.8 out of 10, (112)
"Poorly cleaned and not kept up well."
The price is ₩150,743
₩176,956 total
includes taxes & fees
Jul 16 - Jul 17
Skylark Motel
Freehand Chicago
Relax in style with plush seating and a classic design, featuring a sofa, armchairs, and a bookshelf.

Freehand Chicago

4.0 star property
8.0 out of 10, Very Good, (2074)
"Stayed many times, great fun!"
The price is ₩154,338
₩205,528 total
includes taxes & fees
Aug 6 - Aug 7
Freehand Chicago
The Chicago Hotel Collection - Magnificent Mile
Experience the vibrant city atmosphere from this unique, circular building with a glass facade offering a glimpse into the interior.

The Chicago Hotel Collection - Magnificent Mile

4.0 star property
7.2 out of 10, Good, (1105)
"We enjoyed our time at this stay. "
The price is ₩46,053
₩248,780 total
includes taxes & fees
Jul 27 - Jul 28
The Chicago Hotel Collection - Magnificent Mile
The Hoxton Chicago
Enjoy a casual dining experience with comfortable seating and a variety of beverages.

The Hoxton Chicago

4.0 star property
9.0 out of 10, Wonderful, (1012)
"Excellent location and great vibe. "
The price is ₩289,039
₩339,305 total
includes taxes & fees
Aug 10 - Aug 11
The Hoxton Chicago
FOUND Hotel Chicago River North
Experience the vibrant atmosphere of this historic building, featuring ornate details and a lively dining and entertainment area.

FOUND Hotel Chicago River North

2.0 star property
8.0 out of 10, Very Good, (124)
"Good hotel "
The price is ₩182,620
₩214,377 total
includes taxes & fees
Aug 6 - Aug 7
FOUND Hotel Chicago River North
The Chicago Hotel Collection River North
Enjoy a casual coffee break in our cozy coffee shop with a menu board, seating area, and unique decor.

The Chicago Hotel Collection River North

3.0 star property
7.2 out of 10, Good, (515)
"The rooms were excellent"
The price is ₩105,174
₩236,989 total
includes taxes & fees
Jul 22 - Jul 23
The Chicago Hotel Collection River North
Travelodge by Wyndham Downtown Chicago
Relax in the hotel lobby's spacious seating area, surrounded by a city view and comfortable sofas and armchairs.

Travelodge by Wyndham Downtown Chicago

2.0 star property
7.2 out of 10, Good, (2245)
"Great value for the cost. Pleasant room and facilities, and very friendly and helpful staff. Will stay there again. "
The price is ₩177,987
₩208,939 total
includes taxes & fees
Aug 4 - Aug 5
Travelodge by Wyndham Downtown Chicago
Crowne Plaza Chicago West Loop by IHG
Relax in a casual, urban setting with seating areas and a prominent counter for ordering.

Crowne Plaza Chicago West Loop by IHG

3.5 star property
9.0 out of 10, Wonderful, (1264)
"Great location and hotel "
The price is ₩203,572
₩238,973 total
includes taxes & fees
Aug 10 - Aug 11
Crowne Plaza Chicago West Loop by IHG
Thompson Chicago, by Hyatt
Stairs lead to a bar area with a counter and seating on the upper level.

Thompson Chicago, by Hyatt

4.5 star property
9.0 out of 10, Wonderful, (1165)
"Great location and property!"
The price is ₩198,040
₩273,277 total
includes taxes & fees
Aug 10 - Aug 11
Thompson Chicago, by Hyatt
LondonHouse Chicago, Curio Collection by Hilton
Contemporary lounge area with a striking metal structure and large windows offering urban views.

LondonHouse Chicago, Curio Collection by Hilton

4.5 star property
9.4 out of 10, Exceptional, (3324)
"Great stay"
The price is ₩233,928
₩274,607 total
includes taxes & fees
Aug 10 - Aug 11
LondonHouse Chicago, Curio Collection by Hilton
Millennium Knickerbocker Chicago
Experience the grandeur of our lobby, featuring a stunning chandelier, comfortable seating, and a beautiful staircase.

Millennium Knickerbocker Chicago

4.0 star property
8.6 out of 10, Excellent, (1869)
"Great location near bars and restaurants "
The price is ₩175,636
₩238,651 total
includes taxes & fees
Aug 13 - Aug 14
Millennium Knickerbocker Chicago
Holiday Inn Express Chicago - Magnificent Mile by IHG
Hotel facade with a balcony featuring a variety of flowers and large windows with metal railings.

Holiday Inn Express Chicago - Magnificent Mile by IHG

2.5 star property
8.4 out of 10, Very Good, (1009)
"Excellent area of Chicago with dining and shopping "
The price is ₩192,508
₩225,976 total
includes taxes & fees
Aug 10 - Aug 11
Holiday Inn Express Chicago - Magnificent Mile by IHG
Best Western Grant Park Hotel
Relax in a stylish seating area with plush armchairs and a decorative partition, surrounded by ambient lighting and a patterned rug.

Best Western Grant Park Hotel

2.5 star property
8.2 out of 10, Very Good, (2566)
"Location was excellent."
The price is ₩198,662
₩233,211 total
includes taxes & fees
Aug 11 - Aug 12
Best Western Grant Park Hotel
citizenM Chicago Downtown
Experience the vibrant city atmosphere in this urban oasis, featuring a striking geometric-patterned awning and modern architecture.

citizenM Chicago Downtown

4.0 star property
9.4 out of 10, Exceptional, (3362)
"Great location- fun hotel"
The price is ₩245,671
₩288,394 total
includes taxes & fees
Aug 4 - Aug 5
citizenM Chicago Downtown
Hotel Felix River North/Magnificent Mile
Relax in the hotel lobby, featuring a spacious seating area with a sofa, armchairs, and a small table.

Hotel Felix River North/Magnificent Mile

4.0 star property
8.2 out of 10, Very Good, (1868)
"Great location "
The price is ₩155,860
₩225,171 total
includes taxes & fees
Aug 4 - Aug 5
Hotel Felix River North/Magnificent Mile
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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Learn more about Southwest Side

Explore attractions like Balzekas Museum of Lithuanian Culture and S.S. Peter and Paul Church as you discover things to see and do in Southwest Side.

See all hotels in Southwest Side
Chicago, IL featuring interior views and an airport as well as a couple
Photo by by Midway Intl Airport
Open Photo by by Midway Intl Airport

Top Southwest Side Hotel Reviews

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent
"We arrived super late from a very delayed flight and the staff was so accomodating as I was with my 2 young daughters. They checked us in quickly. Hotel was great and will stay there more often as everyone was super friendly and knowledgeable"
salvatore 2-night trip
Posted 4 hours ago
InterContinental Chicago Magnificent Mile by IHG