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Check availability on Southwest Side 4 Star Hotels

Tonight
6 Oct - 7 Oct
Tomorrow
7 Oct - 8 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for Southwest Side 4-star hotels

A marble-floored lobby with double doors and elevators, each marked with a 'CQ' sign.
A man in a suit sitting by a window with a vase of red flowers.
A hotel entrance with a sign for the Club Quarters Hotel, number 75, and a River Hotel sign.
A conference room with a long table, chairs, and a vase.

1. River Hotel

River Hotel
Downtown Chicago
United States
Jared
£150
includes taxes & fees
1 Nov - 2 Nov
River Hotel
A spacious lobby with a central coffee table, sofas, and a large mirror.
A spacious lobby with high ceilings, large arched windows, and a grand staircase.
A spacious lobby with a grand fireplace, elegant columns, and a seating area with chairs and a table.
A balcony with a table set for a meal, featuring a charcuterie board and two glasses of wine, overlooking a cityscape.

2. The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
Downtown Chicago
United States
Marta
£129
includes taxes & fees
1 Nov - 2 Nov
The Chicago Hotel Collection Ambassador Gold Coast
A grand lobby with a central bar, high ceilings, and classical architecture.
A spacious lobby with a grand chandelier, a fireplace, and elegant seating arrangements.
A modern living room with a sofa set, ottoman, and armchairs.
A grand hallway with ornate ceiling, chandeliers, and a reception desk at the end.

3. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Downtown Chicago
United States
Yesenia
£165
includes taxes & fees
25 Oct - 26 Oct
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
A large, historic building with a central courtyard surrounded by trees.
A marina with numerous boats docked, surrounded by a cityscape with high-rise buildings and a stadium.
A modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.
A hotel room with two beds, a desk with a television, a chair, a desk lamp, and a painting on the wall.

4. Hilton Chicago

Hilton Chicago
Downtown Chicago
Canada
Anna
£171
includes taxes & fees
30 Oct - 31 Oct
Hilton Chicago
An outdoor rooftop lounge with seating, a fire feature, and a view of the city skyline at night.
The Chicago Hotel Collection building with a glass facade, American flag, and signage for Barista Bar and Seighity events.
A modern lobby with a wooden ceiling, leather sofas, and a coffee bar.
A modern lounge area with leather sofas, wooden coffee tables, and ambient lighting.

5. The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
Downtown Chicago
United Kingdom
Jake
£123
includes taxes & fees
1 Nov - 2 Nov
The Chicago Hotel Collection - Magnificent Mile
The Intercontinental hotel facade with a large American flag and a floral display.
A person sitting by a window with a cityscape view.
A swimming pool area with a glass-bottomed pool, a high ceiling with hanging lights, and a staircase with people sitting on it.
A person lying on a bed with a bottle of champagne, surrounded by food and a magazine.

6. InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
United States
Kenan
£217
includes taxes & fees
31 Oct - 1 Nov
InterContinental Chicago Magnificent Mile by IHG
A person relaxing on a sofa with a laptop, a glass of red wine, and a small table with a vase of flowers and a telephone.
A modern hotel lobby with leather sofas, a coffee table, and a floor lamp.
A room with a bed against a window overlooking a cityscape. There is a small table with a book, a vase with flowers, and a cup.
A bar area with a long counter, multiple shelves of bottles, and four bar stools.

7. L7 Chicago by LOTTE

L7 Chicago by LOTTE
Downtown Chicago
United States
Jeffrey Thomas
£162
includes taxes & fees
1 Nov - 2 Nov
L7 Chicago by LOTTE
A person pouring champagne into a glass near a window overlooking a cityscape with a Ferris wheel.
A modern bar area with high stools, a bar counter, and shelves of liquor bottles.
A rooftop terrace with a view of a beach and a Ferris wheel, featuring lounge chairs and a colorful mural.
A modern hotel lobby with a large sign reading "THE WADE," a spacious area with a patterned floor, large windows offering views, and potted plants.

8. The Wade

The Wade
Downtown Chicago
United States
Erin
£128
includes taxes & fees
1 Nov - 2 Nov
The Wade
A modern building with a glass facade and a curved structure.
A reception area with a marble wall, multiple reception counters, and a modern design.
A conference room with a long table, purple chairs, and framed pictures on the walls.
A well-lit grocery store with shelves stocked with snacks and beverages, a checkout counter, and a clean, tiled floor.

9. Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago
Rosemont
United States
Christian
£138
includes taxes & fees
23 Oct - 24 Oct
Hyatt Regency O'Hare Chicago
A spacious bar area with high ceilings and large windows, offering views of a cityscape.
A hotel room with a bed, a sofa with cushions, a large window with a view of a cityscape and water.
A bar with a circular liquor display, seating with stools, and a city view through large windows.
A cityscape with modern high-rise buildings, a river, and a boat.

10. Hyatt Regency Chicago

Hyatt Regency Chicago
Downtown Chicago
United States
Mercy
£249
includes taxes & fees
31 Oct - 1 Nov
Hyatt Regency Chicago
A couple sitting on a blue couch with a table in front of them, holding drinks and a pizza.
A person sitting on a blue couch with a dog beside them, holding a glass of wine, and a pizza on a wooden board on a table.
A modern interior with a dining area, sofas, and artwork on the walls.
A laundry area with a washing machine, a dryer, and an ice dispenser.

11. Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile
Downtown Chicago
United States
Adhba
£101
includes taxes & fees
3 Nov - 4 Nov
Hotel Saint Clair- Magnificent Mile
A modern kitchen with a marble island, fruit bowls, and a city view.
A modern hotel room with a city view, a seating area with two sofas and a coffee table, and a dining area with a table and chairs.
A modern bar area with a central bar, seating, and a distinctive ceiling design.
A modern lounge area with a central bar, seating arrangements, and a decorative chandelier.

12. Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
Downtown Chicago
United States
Ruby
£194
includes taxes & fees
31 Oct - 1 Nov
Fairmont Chicago at Millennium Park
A long, narrow hallway with a patterned carpet, recessed lighting, and doors on one side.
A modern bar area with a curved ceiling, wooden slats, and a bar counter with stools.
A modern interior with a wall-mounted fireplace and a decorative rock installation.
A restaurant interior with a stone accent wall, a bar area, and a seating section.

13. Loews Chicago O'Hare Hotel

Loews Chicago O'Hare Hotel
Rosemont
United States
MARY
£189
includes taxes & fees
23 Oct - 24 Oct
Loews Chicago O'Hare Hotel
A hotel lobby with a reception desk, seating area, and a refrigerator.
A multi-story hotel with a prominent red and white sign on the corner, surrounded by trees and a body of water.
A hotel lobby with a bar, seating area, and large windows.
An indoor swimming pool with clear glass ceilings, lounge chairs, and potted plants.

14. DoubleTree by Hilton Lisle Naperville

DoubleTree by Hilton Lisle Naperville
Naperville
United States
Gaurav
£72
includes taxes & fees
18 Oct - 19 Oct
DoubleTree by Hilton Lisle Naperville
A dining area with a table set for four, large windows offering a cityscape view at dusk.
A modern interior with a central fireplace, seating area, and wall-mounted lighting.
A high-rise hotel room with large windows offering a city view, round tables set for dining, and elegant decor with flowers and candles.
A breakfast table with croissants, a bowl of berries, a glass of orange juice, and a smoothie, set against a cityscape view through a window.

15. The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown
Downtown Chicago
United States
ShaRona
£199
includes taxes & fees
3 Nov - 4 Nov
The Royal Sonesta Chicago Downtown
A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.
A modern living room with a fireplace, leather sofas, and a wooden floor.
A modern lobby with leather sofas, a wooden coffee table, a TV mounted on the wall, and a bookshelf.
A hotel room with a large bed, a TV, a desk, and a chair.

16. Central Loop Hotel

Central Loop Hotel
Downtown Chicago
United States
Nathan
£114
includes taxes & fees
2 Nov - 3 Nov
Central Loop Hotel
A historic building with a prominent casino sign, surrounded by modern skyscrapers.
A modern interior with a round table, four chairs, a vase with flowers, and a view of the street through large windows.
A conference room with tables, chairs, and large windows offering views of the street and buildings outside.
A person pouring a drink into a glass with ice and an orange slice garnish.

17. Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile
Downtown Chicago
United Kingdom
Ian
£122
includes taxes & fees
25 Oct - 26 Oct
Hotel Felix River North/Magnificent Mile
A multi-level atrium with a central spiral staircase, multiple seating areas, and a pool.
A swimming pool with a glass wall, a seating area with sofas, and an exit sign.
A multi-story hotel with a prominent 'Embassy Suites' sign, a Starbucks Coffee shop, and a well-lit street at night.
A multi-level indoor area with a central water feature, surrounded by seating areas and greenery.

18. Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North
Downtown Chicago
United States
Eliana
£152
includes taxes & fees
1 Nov - 2 Nov
Embassy Suites by Hilton Chicago Downtown River North
A hotel room with a sofa, armchairs, a dining table, and a view of the city at night.
A bar area with a bar counter, multiple chairs, and a chandelier.
A terrace with outdoor seating, a view of a control tower, and flags.
A modern lobby with a geometric patterned floor, large windows, and a reception desk with computers.

19. Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport
O'Hare
United States
Richard
£181
includes taxes & fees
30 Oct - 31 Oct
Hilton Chicago O'Hare Airport
A rooftop terrace with outdoor seating, a view of the city skyline, and a river.
A modern living room with a sofa, coffee table, and ottoman, a fireplace, and a large window with a city view.
A modern room with a view of a river and high-rise buildings.
A modern hotel room with a desk, a sofa, a coffee machine, a TV, and a unique wall art piece.

20. LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
United States
Sharee
£229
includes taxes & fees
1 Nov - 2 Nov
LondonHouse Chicago, Curio Collection by Hilton
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Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Southwest Side.
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

120 East Delaware Place Chicago IL
£472
1 Nov - 2 Nov
includes taxes & fees
Four Seasons Hotel Chicago
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

401 N Wabash Ave Chicago IL
£415
1 Nov - 2 Nov
includes taxes & fees
9.6/10 Exceptional! (2,033 reviews)
Trump International Hotel & Tower Chicago
The Langham, Chicago

The Langham, Chicago

330 North Wabash Avenue Chicago IL
£482
1 Nov - 2 Nov
includes taxes & fees
9.8/10 Exceptional! (1,003 reviews)
The Langham, Chicago
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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.

Learn more about Southwest Side

Explore attractions like Balzekas Museum of Lithuanian Culture and Ephraim Bajar Cultural Center as you discover things to see and do in Southwest Side.

See all hotels in Southwest Side
An airport with multiple runways, parked airplanes, and a large terminal building.
Photo by by Midway Intl Airport

Top Southwest Side Hotel Reviews

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"Great stay for a few days. Very convenient location and close to the train. Rooftop bars are also great, shout out to the staff"
Joel 3-night trip
Posted 1 hour ago
The Chicago Hotel Collection - Magnificent Mile
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good
"Great location and there is parking close by in a garage for $40 per night. The hotel itself is nice but the room we stayed in had stained carpets and couch cushions. Assuming all rooms are alike, rooms need a deep clean and some updates. Overall, pretty solid stay if you’re on a budget but want to stay in a quiet and old-money neighborhood"
Yevgeniy 4-night trip
Posted 2 hours ago
The Chicago Hotel Collection Ambassador Gold Coast
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

8/10 Good
"There was no place to hang clothes in our very small room. The feather pillows were comfortable. The AC fan can be run continuously to drown out the nearby EL. We had a $2000 plus hold placed on our credit card even though we prepaid for the room."
Michael Scott 6-night trip
Posted 3 hours ago
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

8/10 Good
"No fridge and pretty thin walls but a good property"
Avery 2-night trip
Posted 3 hours ago
Club Quarters Hotel, Central Loop, Chicago
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

10/10 Excellent
"NO breakfast available"
SERGIO AGUSTIN 3-night trip
Posted 7 hours ago
Hotel Saint Clair- Magnificent Mile
Hilton Chicago

Hilton Chicago

10/10 Excellent
"A bit on the older end but in very good shape despite it's age. Huge hotel, very fast elevators which is a big bonus. No waiting. Great location and awesome for a Bears game."
Ethan 1-night trip
Posted 8 hours ago
Hilton Chicago

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