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7 Aug - 8 Aug
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8 Aug - 9 Aug
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8 Aug - 10 Aug
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Top 10 Southwest Side hotels and places to stay

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, (2057)
"Beautiful property, will definitely stay there again."
The price is ฿5,773
฿7,716 total
includes taxes & fees
1 Sept - 2 Sept
Sable at Navy Pier Chicago, Curio Collection by Hilton
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, (1065)
"Great place to stay, would definitely recommend and stay here again "
The price is ฿1,354
฿6,146 total
includes taxes & fees
11 Aug - 12 Aug
The Chicago Hotel Collection Ambassador Gold Coast
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, (2167)
"Good spot when staying for lolla "
The price is ฿3,611
฿4,809 total
includes taxes & fees
20 Aug - 21 Aug
Freehand Chicago
Rainbow Motel
Relax in a serene bedroom with a large bed, minimalist decor, and a cityscape painting above.

Rainbow Motel

2.5 star property
5.4 out of 10, (8)
"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 ฿2,894
฿3,397 total
includes taxes & fees
20 Aug - 21 Aug
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
6.4 out of 10, (1002)
"Staff are very friendly:) "
The price is ฿3,388
฿3,977 total
includes taxes & fees
19 Aug - 20 Aug
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
4.6 out of 10, (114)
"A dump. Next time im forced to choose this place or a floor in the airport, I'll choose the floor."
The price is ฿3,527
฿4,140 total
includes taxes & fees
20 Aug - 21 Aug
Skylark Motel
The Chicago Hotel Collection - Magnificent Mile
Relax in a serene urban setting with a spacious seating area and unobstructed city views.

The Chicago Hotel Collection - Magnificent Mile

4.0 star property
7.4 out of 10, Good, (1139)
"Enjoyed staying here!"
The price is ฿1,078
฿5,821 total
includes taxes & fees
11 Aug - 12 Aug
The Chicago Hotel Collection - Magnificent Mile
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, (1279)
"A wonderful hotel in a great location!"
The price is ฿9,582
฿12,197 total
includes taxes & fees
8 Aug - 9 Aug
Claridge House
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, (2573)
"The walkability was great & even with a packed hotel, the staff was very accommodating & it was quiet."
The price is ฿3,823
฿4,488 total
includes taxes & fees
25 Aug - 26 Aug
Best Western Grant Park Hotel
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, (2277)
"Hotel location, staff and transportation were very good "
The price is ฿3,087
฿3,624 total
includes taxes & fees
25 Aug - 26 Aug
Travelodge by Wyndham Downtown Chicago
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, (543)
"It was a wonderful place to stay! "
The price is ฿2,184
฿5,220 total
includes taxes & fees
19 Aug - 20 Aug
The Chicago Hotel Collection River North
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, (1930)
"Great stay"
The price is ฿4,110
฿5,584 total
includes taxes & fees
24 Aug - 25 Aug
Millennium Knickerbocker Chicago
Swissotel - Chicago
Enjoy a panoramic city view from this stylish room, featuring a spacious dining area with a round table and six comfortable chairs.

Swissotel - Chicago

4.5 star property
8.8 out of 10, Excellent, (2553)
"Hotel is amazing "
The price is ฿4,911
฿6,715 total
includes taxes & fees
1 Sept - 2 Sept
Swissotel - Chicago
Ohio House Motel
Located at the corner of a bustling street, Ohio House features a flat roof and large glass windows.

Ohio House Motel

3.0 star property
9.0 out of 10, Wonderful, (1002)
"Great place to stay!"
The price is ฿4,271
฿5,014 total
includes taxes & fees
24 Aug - 25 Aug
Ohio House Motel
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, (1001)
"Excellent location and great vibe. "
The price is ฿7,087
฿8,319 total
includes taxes & fees
17 Aug - 18 Aug
The Hoxton Chicago
Central Loop Hotel
Enjoy casual dining in a rustic setting with exposed brick walls and wooden furniture.

Central Loop Hotel

4.0 star property
8.6 out of 10, Excellent, (1805)
"Enjoyed our stay"
The price is ฿5,382
฿6,318 total
includes taxes & fees
17 Aug - 18 Aug
Central Loop Hotel
River Hotel
Elevators lead to upper floors from this grand corridor, flanked by ornate columns.

River Hotel

4.0 star property
8.8 out of 10, Excellent, (4490)
"Great place to stay."
The price is ฿5,404
฿6,344 total
includes taxes & fees
17 Aug - 18 Aug
River Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Experience the sleek, modern architecture of this urban hotel, featuring a prominent marquee sign and vertical windows.

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
8.4 out of 10, Very good, (3631)
"Great stay. "
The price is ฿4,785
฿5,617 total
includes taxes & fees
24 Aug - 25 Aug
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Best Western River North Hotel
Relax on the rooftop with wicker lounge chairs and take in the city skyline views.

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1025)
"Great location "
The price is ฿4,098
฿4,811 total
includes taxes & fees
24 Aug - 25 Aug
Best Western River North Hotel
Bluegreen Vacations Hotel Blake, Ascend Resort Collection
Exterior

Bluegreen Vacations Hotel Blake, Ascend Resort Collection

4.0 star property
9.6 out of 10, Exceptional, (1005)
"Clean, large rooms, very comfortable."
The price is ฿5,474
฿6,425 total
includes taxes & fees
21 Aug - 22 Aug
Bluegreen Vacations Hotel Blake, Ascend Resort Collection
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
Photo by by Midway Intl Airport
Open Photo by by Midway Intl Airport

Top Southwest Side Hotel Reviews

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"Love everything about the hotel. Except the costumer service and housekeeping, they was punching me, before the time ⏲️ of my check out "
Gissella P Mejia 3-night trip
Posted 18 hours ago
Hilton Chicago/Magnificent Mile Suites