Lodging Image

Compare and book 4 Star hotels in Southwest Side, Chicago

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

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 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.
A hotel room with a grey sofa, a bed with a white mattress, a wooden dresser, and a large window with curtains.

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 spacious lounge area with leather sofas, round tables, and comfortable chairs, featuring a wooden ceiling and elegant decor.

2. The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
Downtown Chicago
United States
Marta
£112
includes taxes & fees
7 Oct - 8 Oct
The Chicago Hotel Collection Ambassador Gold Coast
A grand lobby with a central bar, high ceilings, and classical architecture.
A modern living room with a round dining table, bar stools, a purple armchair, and a sofa with cushions.
A grand hallway with ornate ceiling, chandeliers, and a reception desk at the end.
A spacious lobby with a grand chandelier, a fireplace, and elegant seating arrangements.

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 restaurant interior with wooden tables and chairs, a carpeted floor, and framed pictures on the walls.
A hotel room with two beds, a desk with a television, a chair, a desk lamp, and a painting on the wall.
A modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.

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.
A modern lounge area with leather sofas, wooden coffee tables, and ambient lighting.
A rooftop venue with white chairs and a sofa, draped with white fabric and floral arrangements, overlooking a cityscape.
A modern lobby with a wooden ceiling, leather sofas, and a coffee bar.

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 lying on a bed with a bottle of champagne, surrounded by food and a magazine.
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.

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 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 modern hotel lobby with leather sofas, a coffee table, and a floor lamp.
A modern restaurant with high ceilings, wooden flooring, and a central chandelier. Tables are set with wine glasses and red cushions.

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 hotel lobby with a marble floor, seating areas, and a ceiling with a sky-like projection.
A modern hotel room with a large window offering a view of the sea and a cityscape. There is a seating area with a sofa and a small table.
A modern bar area with high stools, a bar counter, and shelves of liquor bottles.

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 well-lit grocery store with shelves stocked with snacks and beverages, a checkout counter, and a clean, tiled floor.
A reception area with a marble wall, multiple reception counters, and a modern design.
A woman running on a treadmill in a gym with another person in the background.

9. Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago
Rosemont
United States
Christian
£138
includes taxes & fees
24 Oct - 25 Oct
Hyatt Regency O'Hare Chicago
A spacious bar area with high ceilings and large windows, offering views of a cityscape.
A bar with a circular liquor display, seating with stools, and a city view through large windows.
A multi-level hotel lobby with a glass elevator, a seating area, and a dining space.
A hotel room with a bed, a sofa with cushions, a large window with a view of a cityscape and water.

10. Hyatt Regency Chicago

Hyatt Regency Chicago
Downtown Chicago
United States
Mark
£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 modern interior with a dining area, sofas, and artwork on the walls.
A hotel room with two beds, a window with curtains, a bedside table with a lamp, and a small ottoman.
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.

11. Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile
Downtown Chicago
United States
Adhba
£101
includes taxes & fees
2 Nov - 3 Nov
Hotel Saint Clair- Magnificent Mile
A modern kitchen with a marble island, fruit bowls, and a city view.
A modern lounge area with a central bar, seating arrangements, and a decorative chandelier.
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 Fairmont hotel with a prominent entrance, large windows, and a sculpture on the facade.

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.
Exterior

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 conference room with a large table, chairs, and large windows offering a view of trees and a pond.
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.

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 breakfast table with croissants, a bowl of berries, a glass of orange juice, and a smoothie, set against a cityscape view through a window.
A modern interior with a central fireplace, seating area, and wall-mounted lighting.
A rooftop terrace with outdoor seating and a fire pit, overlooking a cityscape with tall buildings.

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 person sitting on a couch with a laptop, reading a book, in a room with a large window and a framed picture on the wall.
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.

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 person pouring a drink into a glass with ice and an orange slice garnish.
A hotel room with two beds, a dining table with chairs, a city view, and a minibar.

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 spacious lobby with a central staircase, multiple floors, a reception desk, and seating areas.
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.

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 modern lobby with a geometric patterned floor, large windows, and a reception desk with computers.
A terrace with outdoor seating, a view of a control tower, and flags.
A restaurant with a central round table surrounded by chairs, a buffet counter with food and drinks, and a large window with a cityscape view.

19. Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport
O'Hare
United States
Samuel
£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 hotel room with a large bed, a desk, a sofa, and a view of the city.
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
£230
includes taxes & fees
1 Nov - 2 Nov
LondonHouse Chicago, Curio Collection by Hilton
Save an average of 15% on thousands of hotels when you're signed in

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
9.4/10 Exceptional! (1,004 reviews)
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! (2,046 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
Still don't see what you're looking for?
See all properties in Southwest Side.
You can also use these popular filters to refine your search.
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

River Hotel

River Hotel

10/10 Excellent
"Friendly staff, older hotel but clean rooms. Appreciate the noon checkout. Great location."
Krystel 3-night trip
Posted less than an hour ago
River Hotel
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

10/10 Excellent
"NO breakfast available"
SERGIO AGUSTIN 3-night trip
Posted 1 hour 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 1 hour ago
Hilton Chicago
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent
"beautful. clean"
Tony 2-night trip
Posted 1 hour ago
The Chicago Hotel Collection Ambassador Gold Coast
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

8/10 Good
"Location is great for downtown. Valet parking is pricey - $80/night. Room was spacious, clean and the bathroom was plenty big. However, I returned one night around 1 a.m. and was met with "I need to see your I.D....What room are you in?" I found this a bit off-putting, as I have never had to do this at any other property around the world in far more prestigious hotels. It left a bit of a bad taste in my mouth on Royal Sonesta...."
Nathan 3-night trip
Posted 1 hour ago
The Royal Sonesta Chicago Downtown
Hyatt Regency Chicago

Hyatt Regency Chicago

8/10 Good
"Better organize breakfast hours: often we had long line in buffet and waiting time ~10-15min. For morning hours - it's unacceptable"
Aleksandr 5-night trip
Posted 2 hours ago
Hyatt Regency Chicago
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

10/10 Excellent
"very helpful staff, large rest areas for waiting, good price, convenient location. A nice no-frills restaurant and bar onsite. Best choice for an Unpretentious visit stay."
Yang 4-night trip
Posted 19 hours ago
Club Quarters Hotel, Central Loop, Chicago

Find out more about Southwest Side

Explore a world of travel with Expedia