Southwest Side

Travel Guide

Photo provided by by Midway Intl Airport
Photo provided by by Midway Intl Airport
Photo provided by by Midway Intl Airport
Photo provided by by Midway Intl Airport
Photo provided by by Midway Intl Airport
Photo provided by by Midway Intl Airport
Photo provided by by Midway Intl Airport
Photo provided by by Midway Intl Airport
Photo provided by by Midway Intl Airport
Photo provided by by Midway Intl Airport

Where to stay in Southwest Side

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Back of the Yards

While there might not be top attractions in Back of the Yards, you can explore the larger area and discover places like Bridgeport Art Center and Zhou B Art Center.

Back of the Yards
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Garfield Ridge

Be sure to check out the restaurants and churches while you're strolling through Garfield Ridge, and hop on the metro at Midway Station to see more of the surrounding area.

Garfield Ridge
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McKinley Park

Be sure to check out the monuments and shopping while you're strolling through McKinley Park, and hop on the metro at 35th-Archer Station to see more of the surrounding area.

McKinley Park
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Brighton Park

The restaurants and shopping are a few reasons travellers visit Brighton Park. Though there aren't many top sights in the neighbourhood, you can visit United Center and Bridgeport Art Center, a few notable attractions nearby.

Brighton Park
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New City

Beaches and mountain views are just a few things travellers like about New City. A stop by Union Stock Yard Gate is also recommended if you've got time to explore the area.

New City
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West Lawn

Travellers enjoy West Lawn for its restaurants and museums. Consider checking out Balzekas Museum of Lithuanian Culture while you're in the area.

West Lawn
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (9,385 reviews)
"This is a beautiful historic Chicago downtown hotel across the street from Grant Park. However, some of the rooms and hallways are in need of updating."

Reviewed on 1 Oct, 2025

Get rates
Congress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
The price is S$185 per night from 27 Oct to 28 Oct
S$185
27 Oct - 28 Oct
includes taxes & fees
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
7.8/10 Good! (2,417 reviews)
Good for 3 nights
"The price was right, the location excellent for shopping, riverwalk, other attractions within walking distance. The rooms are tiny, the bar and breakfast inconsistent. The mattress was terrible and needs to be replaced. The lobby area is beautifully refurbished and a place to spend time reading, ..."

Reviewed on 30 Sept, 2025

Freehand Chicago
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
The price is S$256 per night from 5 Nov to 6 Nov
S$256
5 Nov - 6 Nov
includes taxes & fees
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.4/10 Very Good! (5,020 reviews)
"Hotel is great and they were very attentive to anything that was needed. I cant say enough about the staff. Chicago is one of this country's great walkable cities so the location provided great opportunity to easier get where you want to go."

Reviewed on 1 Oct, 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,939 properties in Southwest Side
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.
Sentral Michigan Avenue

Sentral Michigan Avenue

4 out of 5
808 SOUTH MICHIGAN AVENUE, Chicago, IL
Stay at this 4-star business-friendly aparthotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the ...
9/10 Wonderful! (948 reviews)
"Great location and cleanliness of rooms. Staff was extremely helpful"

Reviewed on 4 Oct, 2025

Sentral Michigan Avenue
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4 out of 5
One Superior Place, Chicago, IL
Stay at this 4-star aparthotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
9.2/10 Wonderful! (552 reviews)
"Larger bed would be nice, but everything else was great. Thank you!"

Reviewed on 6 Oct, 2025

Kasa Magnificent Mile Chicago
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
1140 North Wells Street, Chicago, IL
Stay at this 4-star family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our ...
8.8/10 Excellent! (361 reviews)
"Everything was wonder beside my shower head it was leaking bad"

Reviewed on 30 Sept, 2025

Level Chicago – Old Town
See all properties in Southwest Side
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.

Popular places to visit

Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
Magnificent Mile - River North featuring street scenes, night scenes and signage

Michigan Avenue

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier

Navy Pier

A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.

Navy Pier
McCormick Place

McCormick Place

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Millennium Park which includes modern architecture, a city and autumn leaves

Millennium Park

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park
Soldier Field showing a city, modern architecture and a skyscraper

Soldier Field

Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.

Soldier Field

Things to do

River tour boat in Chicago

Architecture River Tour

S$63
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

S$57
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

S$32
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

S$58
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

S$58
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
Relax and enjoy the view

Chicago Architecture Center River Cruise aboard First Lady

S$72
per adult
96% of travellers recommend
Chicago Architecture Center River Cruise aboard First Lady
See all activities in Southwest Side
Chicago which includes a city and a high-rise building as well as a family

Chicago