Lodging Image

4 Star Hotels in Southwest Side, Chicago

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Southwest Side 4 Star Hotels

Tonight
28 Sept - 29 Sept
Tomorrow
29 Sept - 30 Sept
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 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 room with a grey sofa, a bed with a white mattress, a wooden dresser, and a large window with curtains.
A conference room with a long table, chairs, and a vase.
A man in a suit sitting by a window with a vase of red flowers.

1. River Hotel

River Hotel
Downtown Chicago
United States
Jared
€194
includes taxes & fees
25 Oct - 26 Oct
River Hotel
A spacious lobby with a central coffee table, sofas, and a large mirror.
A spacious lobby with a grand fireplace, elegant columns, and a seating area with chairs and a table.
A spacious lobby with high ceilings, large arched windows, and a grand staircase.
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
€187
includes taxes & fees
14 Oct - 15 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 spacious lobby with a grand chandelier, a fireplace, and elegant seating arrangements.
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
Amanda
€208
includes taxes & fees
4 Oct - 5 Oct
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
A large, historic building with a central courtyard surrounded by trees.
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.
A marina with numerous boats docked, surrounded by a cityscape with high-rise buildings and a stadium.

4. Hilton Chicago

Hilton Chicago
Downtown Chicago
United States
Alan
€193
includes taxes & fees
24 Oct - 25 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 rooftop venue with white chairs and a sofa, draped with white fabric and floral arrangements, overlooking a cityscape.
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 States
Lauryn
€168
includes taxes & fees
25 Oct - 26 Oct
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 bar area with a high bar counter, multiple stools, and a seating area with booths and tables.

6. InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
United States
Kenan
€305
includes taxes & fees
25 Oct - 26 Oct
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
Emily
€284
includes taxes & fees
25 Oct - 26 Oct
L7 Chicago by LOTTE
A person pouring champagne into a glass near a window overlooking a cityscape with a Ferris wheel.
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 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.

8. The Wade

The Wade
Downtown Chicago
United States
Fernanda
€156
includes taxes & fees
25 Oct - 26 Oct
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 conference room with a long table, purple chairs, and framed pictures on the walls.
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
Alison
€179
includes taxes & fees
18 Oct - 19 Oct
Hyatt Regency O'Hare Chicago
A spacious bar area with high ceilings and large windows, offering views of a cityscape.
A cityscape with modern high-rise buildings, a river, and a boat.
A multi-level hotel lobby with a glass elevator, a seating area, and a dining space.
A bar with a circular liquor display, seating with stools, and a city view through large windows.

10. Hyatt Regency Chicago

Hyatt Regency Chicago
Downtown Chicago
United States
Whitney
€361
includes taxes & fees
25 Oct - 26 Oct
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 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 hotel room with two beds, a window with curtains, a bedside table with a lamp, and a small ottoman.

11. Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile
Downtown Chicago
United Kingdom
Peter
€176
includes taxes & fees
28 Oct - 29 Oct
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 Fairmont hotel with a prominent entrance, large windows, and a sculpture on the facade.
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
€275
includes taxes & fees
25 Oct - 26 Oct
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 building entrance with a car parked in front.
A modern interior with a wall-mounted fireplace, a rock installation, and a green wall.

13. Loews Chicago O'Hare Hotel

Loews Chicago O'Hare Hotel
Rosemont
United States
MARY
€219
includes taxes & fees
2 Oct - 3 Oct
Loews Chicago O'Hare Hotel
A hotel lobby with a reception desk, seating area, and a refrigerator.
A hotel lobby with a bar, seating area, and large windows.
An indoor swimming pool with clear glass ceilings, lounge chairs, and potted plants.
A conference room with a large table, chairs, and large windows offering a view of trees and a pond.

14. DoubleTree by Hilton Lisle Naperville

DoubleTree by Hilton Lisle Naperville
Naperville
United States
Gaurav
€84
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
€278
includes taxes & fees
29 Oct - 30 Oct
The Royal Sonesta Chicago Downtown
A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.
A hotel room with a large bed, a TV, a desk, and a chair.
A modern lobby with leather sofas, a wooden coffee table, a TV mounted on the wall, and a bookshelf.
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.

16. Central Loop Hotel

Central Loop Hotel
Downtown Chicago
United States
Nathan
€154
includes taxes & fees
25 Oct - 26 Oct
Central Loop Hotel
A historic building with a prominent casino sign, surrounded by modern skyscrapers.
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.
A conference room with tables, chairs, and large windows offering views of the street and buildings outside.

17. Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Netherlands
Shyreen
€191
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-level indoor area with a central water feature, surrounded by seating areas and greenery.
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
€222
includes taxes & fees
26 Oct - 27 Oct
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 bar area with a bar counter, multiple chairs, and a chandelier.
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 Kingdom
Don
€218
includes taxes & fees
24 Oct - 25 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 desk, a sofa, a coffee machine, a TV, and a unique wall art piece.
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.

20. LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
United States
Sharee
€289
includes taxes & fees
25 Oct - 26 Oct
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
€642
4 Oct - 5 Oct
includes taxes & fees
Four Seasons Hotel Chicago
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

401 N Wabash Ave Chicago IL
€544
4 Oct - 5 Oct
includes taxes & fees
9.6/10 Exceptional! (2,034 reviews)
Trump International Hotel & Tower Chicago
The Langham, Chicago

The Langham, Chicago

330 North Wabash Avenue Chicago IL
€627
29 Oct - 30 Oct
includes taxes & fees
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
"Perfect location"
Nikodem 1-night trip
Posted 2 hours ago
River Hotel
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Have a friendly, knowledgeable and polite staff. Hotel in an ideal location, rooms are clean, restaurant in hotel. It's in walking distance to numerous downtown amenities, sights, museums, parks, etc."
Ricky 3-night trip
Posted 3 hours ago
The Royal Sonesta Chicago Downtown
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

8/10 Good
"The staff are definitely the highlight of this hotel. The interior/lobby is BEAUTIFUL and the bar in the lobby was amazing, drinks were very good. Just stayed 1 night, they upgraded my room for free which was very nice but once I got into the room I could immediately tell it was a MUCH older hotel. The decor was outdated, there was also just a bed and a desk chair in the room lol nothing else. Couldn’t sit anywhere that wasn’t the bed…bathroom was okay too. Towels had some stains on them. Other than that it was a decent stay. I’d probably book somewhere else next time just because it’s not as modern as it seemed to be online but if you like the older style hotels definitely check this one out."
Jenna 1-night trip
Posted 6 hours ago
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

10/10 Excellent
"Great location, quiet and spacious"
Yosnina 1-night trip
Posted 18 hours ago
Club Quarters Hotel, Central Loop, Chicago

Explore a world of travel with Expedia