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Southwest Side Hotels

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Our top choices for Southwest Side hotels

Restaurant
Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG
2.5 star property
West Lawn
8.4 out of 10, Very Good, (1000)
"Nice room, chill environment and a super fun staff! Watching the Bears game in the bar was a blast."
United States
Wayne
The price is P6,238
P7,911 total
includes taxes & fees
Jan 4 - Jan 5
Holiday Inn Chicago – Midway Airport S by IHG
Coffee and/or coffee maker
Carlton Inn Midway

Carlton Inn Midway

Carlton Inn Midway
2.0 star property
Archer Heights
6.4 out of 10, (1001)
Located just minutes from Midway Airport, this hotel offers a complimentary shuttle service available 24 hours daily. Enjoy free Wi-Fi, parking, and continental breakfast each morning. The fitness center provides workout options, while Pulaski Station is a 7-minute walk away.
"The room was clean and satisfied our needs. Was handy using their shuttle to Midway Airport."
United States
Charles
The price is P5,452
P6,400 total
includes taxes & fees
Jan 2 - Jan 3
Carlton Inn Midway
Exterior
Skylark Motel

Skylark Motel

Skylark Motel
2.0 star property
Garfield Ridge
4.6 out of 10, (119)
Located in Chicago with easy access to McCormick Place and Wintrust Arena, this motel offers complimentary WiFi and parking. The 24-hour front desk ensures round-the-clock assistance, while Soldier Field and Lake Michigan are just a short drive away.
"Easily one of the worst places ever. Slightly better than spending the night in Chicago Midway terminal."
United States
Stephen
The price is P5,247
P6,159 total
includes taxes & fees
Jan 4 - Jan 5
Skylark Motel
Jetted tub
Rainbow Motel

Rainbow Motel

Rainbow Motel
2.0 star property
Garfield Ridge
5.8 out of 10, (18)
Located within a short drive of Chicago's top attractions, this hotel offers free WiFi and complimentary parking. Enjoy room service after exploring nearby Lake Michigan or catch a game at United Center. SeatGeek Stadium is just minutes away.
"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 "
United States
Conner
The price is P5,708
P7,290 total
includes taxes & fees
Jan 2 - Jan 3
Rainbow Motel
Reception
River Hotel

River Hotel

River Hotel
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (4875)
Strategically positioned near Michigan Avenue, this hotel offers business travelers easy access to Chicago Riverwalk and Millennium Park. Enjoy free WiFi, convenient room service, and a fitness center while Clark-Lake Station is just 7 minutes away.
"Great location, comfortable room, and nice staff."
United States
Claudia
The price is P4,810
P5,647 total
includes taxes & fees
Jan 14 - Jan 15
River Hotel
Cocktail bar
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2994)
Experience modern comfort in downtown Chicago with an indoor pool and on-site American restaurant. Just a 10-minute walk from Michigan Avenue and close to Grand Station, this hotel offers a fitness center and bar for your urban adventure.
"Great place to stay"
United States
Elisha
The price is P5,423
P6,367 total
includes taxes & fees
Jan 18 - Jan 19
Aloft Chicago Mag Mile
Terrace/patio
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2298)
Experience waterfront elegance at this Curio Collection hotel directly on Navy Pier. Just steps from Lake Michigan, guests enjoy Latin flavors at Lirica restaurant, 2 stylish bars, and a 24-hour fitness center. Michigan Avenue shopping and convenient transit options enhance this prime Chicago location.
"Great stay!"
United States
Angela
The price is P5,124
P8,022 total
includes taxes & fees
Jan 20 - Jan 21
Sable at Navy Pier Chicago, Curio Collection by Hilton
Front of property
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3088)
"Excellent stay great location and great rooms"
United States
Joseph
The price is P5,865
P8,544 total
includes taxes & fees
Jan 4 - Jan 5
Hotel Riu Plaza Chicago
Premium bedding, down comforters, pillowtop beds, in-room safe
The Wade

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very Good, (1558)
Experience Chicago's allure at this elegant hotel near Michigan Avenue and Lake Michigan. Guests rave about the quiet rooms, stunning lake views, and proximity to Navy Pier. Enjoy American cuisine at Current restaurant after unwinding in the indoor pool.
"Great staff and great location. "
United States
Joe
The price is P5,452
P6,400 total
includes taxes & fees
Jan 5 - Jan 6
The Wade
Banquet hall
Congress Plaza Hotel

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
Downtown Chicago
8.0 out of 10, Very Good, (9730)
Immerse in this historic Chicago hotel offering majestic lake vistas and beautiful sunrises. Just steps from Columbia College, with 2 restaurants and bars on site. Guests love the central location near public transport and major attractions.
"Wonderful stay!"
United States
Zach
Congress Plaza Hotel
Terrace/patio
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2209)
Located in bustling downtown, this hotel offers stunning city views from select rooms. The outdoor pool and rooftop terrace create a refreshing escape after exploring Michigan Avenue and Chicago Riverwalk. Starbucks in the lobby and Grand Station just 9 minutes away enhance the convenient experience.
"It was a beautiful stay "
United States
Donald
The price is P5,027
P5,902 total
includes taxes & fees
Jan 8 - Jan 9
DoubleTree by Hilton Chicago - Magnificent Mile
Reception
Swissotel - Chicago

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3067)
Indulge in this luxurious Chicago hotel near Millennium Park and Chicago Riverwalk. Enjoy 2 bars, 24-hour fitness center, and The Palm restaurant. Only 10 minutes to Randolph-Wabash Station, with deep-tissue massages and 24-hour room service available.
"Amazing staff and location beautiful hotel "
United States
RANDIE
The price is P6,708
P9,601 total
includes taxes & fees
Jan 23 - Jan 24
Swissotel - Chicago
2 bars/lounges
Hyatt Regency Chicago

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3413)
Immerse yourself in Chicago's energy at this centrally located hotel. Just steps from Michigan Avenue Bridge and Chicago Riverwalk, enjoy 4 restaurants, 2 coffee shops, and stunning city views. Millennium Station is only a 7-minute walk away.
"The Hotel was amazing great location "
United States
Donnisha
The price is P8,474
P11,675 total
includes taxes & fees
Jan 20 - Jan 21
Hyatt Regency Chicago
Ballroom
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3627)
"Great place to stay "
United States
RaShawna
The price is P5,260
P6,175 total
includes taxes & fees
Feb 1 - Feb 2
Hilton Chicago/Magnificent Mile Suites
Lobby sitting area
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2024)
Located in the heart of Chicago, this hotel offers easy access to the Riverwalk and Chicago Theatre. Clean rooms provide comfort after exploring Michigan Avenue and Millennium Park. State Station is just 4 minutes away for convenient city adventures.
"Great stay"
United States
Kramer
The price is P4,810
P5,647 total
includes taxes & fees
Jan 14 - Jan 15
Club Quarters Hotel Wacker at Michigan, Chicago
Lobby sitting area
Warwick Allerton - Chicago

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (3009)
This historic Chicago hotel offers amazing views and a quiet, relaxing atmosphere. Just 6 minutes from Chicago Station and near the Riverwalk, guests enjoy a 24-hour fitness center and convenient bar/lounge after a day of city exploration.
"Every thing is perfect, the location, safe for solo travel. "
United States
Ken
The price is P4,722
P7,273 total
includes taxes & fees
Jan 11 - Jan 12
Warwick Allerton - Chicago
Bar (on property)
voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (3542)
Stylish hotel minutes from Chicago Riverwalk and Merchandise Mart with convenient access to public transit. Relax in the indoor pool, sauna, and bar after exploring Michigan Avenue, or maintain routines at the 24-hour fitness center.
"Great location and breakfast.. can be a bit pricey but worth it. "
Canada
Shaurya
The price is P6,779
P7,958 total
includes taxes & fees
Jan 15 - Jan 16
voco Chicago Downtown - Riverwalk by IHG
Exterior
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1054)
"Clean room, clean hotel, wonderful restaurant/bar. AMAZING location! "
United States
Rebecca
The price is P5,767
P8,497 total
includes taxes & fees
Jan 18 - Jan 19
Hyatt Centric Chicago Magnificent Mile
Breakfast, lunch and dinner served
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (3345)
Experience urban convenience at this downtown hotel, just a 5-minute walk from Willis Tower. The Jackson Station is only 3 minutes away, with Millennium Park and Art Institute within a 10-minute stroll. Enjoy the 24-hour fitness center and on-site restaurant.
"Great hotel "
United States
Anthony
The price is P4,807
P5,643 total
includes taxes & fees
Jan 14 - Jan 15
Club Quarters Hotel, Central Loop, Chicago
Exterior
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Downtown Chicago
8.2 out of 10, Very Good, (2783)
Just a 10-minute walk from Michigan Avenue, this hotel offers free breakfast and room service. Guests can use the fitness center before exploring nearby Chicago Riverwalk and Millennium Park. Grand Station is 8 minutes away.
"Great hotel staff and location. "
United States
Jacqueline
The price is P4,936
P7,525 total
includes taxes & fees
Jan 11 - Jan 12
Embassy Suites by Hilton Chicago Downtown 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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Stay near popular Southwest Side attractions

Marquette Park

After visiting Marquette Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art scene.
See properties

S.S. Peter and Paul Church

After visiting S.S. Peter and Paul Church, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art scene.
See properties

Learn more about Southwest Side

Explore attractions like Balzekas Museum of Lithuanian Culture and Union Stock Yard Gate as you discover things to see and do in Southwest Side.

See all hotels in Southwest Side
Chicago, IL showing interior views, heritage elements and an airport
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
"Staff was very courteous and helpful"
Roy 3-night trip
Posted 5 hours ago
Hilton Chicago/Magnificent Mile Suites

More cheap stays in Southwest Side

Motel 6 Naperville, IL

Motel 6 Naperville, IL

1585 Naperville Wheaton Road Naperville IL
The price is P2,795 per night from Jan 20 to Jan 21
P2,795
P3,115 total
Jan 20 - Jan 21
includes taxes & fees
7.8/10 Good! (1,168 reviews)