Southwest Side, IL

Travel Guide

An airport with multiple runways, parked airplanes, and a large terminal building.
An airplane exhibit labeled "Concourse A" in an airport terminal.
An indoor space with a large airplane model suspended from the ceiling, a sign reading "Concourse A", and a display of various aircraft.
A modern building with a clock tower and a glass facade.
An aircraft's underside with propellers and landing gear, inside a hangar with a high ceiling and windows.

Get to know the Southwest Side with its urban parks, cultural neighborhoods, and opportunities for family-friendly adventures.

Southwest Side is known for its proximity to various urban parks, sports venues, and natural features. Nearby, you can visit Grant Park and Millennium Park, both offering green spaces for relaxation and recreation. For entertainment, Navy Pier serves as a popular destination along the waterfront. Sports enthusiasts can check out several nearby stadiums, including Soldier Field, United Center, and SeatGeek Stadium. If you’re looking for a natural escape, the Ned Brown Forest Preserve is a lake that provides family-friendly entertainment options.

Make sure to explore the distinct neighborhoods surrounding Southwest Side. Chinatown is recognized for its cultural experiences and family-friendly atmosphere, featuring the historic Chinatown Gateway and the Chinese American Museum of Chicago. Another nearby area, West Englewood, is known for its outdoor experiences, making it a great spot for families. Likewise, Hyde Park offers a blend of family and cultural experiences, with notable sites such as the Griffin Museum of Science and Industry, Robie House, and Midway Plaisance.

The best time to visit Southwest Side is from June to September, when the weather is mild and mostly dry, with temperatures ranging from 67 to 73°F. Although the area is generally steady in terms of demand throughout the year, expect a bit more busyness during April and the summer months of June to July. If you prefer quieter times, consider visiting from October to December, when you might find fewer crowds and a more relaxed atmosphere.

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$107 nightly
The price is $127 total per night from Nov 22 to Nov 23
$127 total
Nov 22 - Nov 23
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (10,081 reviews)
"Room stunk very bad staff refused to upgrade or give another room. Unsatisfied stay, DO NOT RECOMMEND."

Reviewed on Nov 14, 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
$116 nightly
The price is $138 total per night from Dec 1 to Dec 2
$138 total
Dec 1 - Dec 2
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
$98 nightly
The price is $117 total per night from Dec 10 to Dec 11
$117 total
Dec 10 - Dec 11
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (5,617 reviews)
"Amazing spot right in the middle of the action, shopping to the north and attractions to the south. The river right beside the hotel and the lake a short walk away. My room was a little tight but I am not in Chicago to be in my room. Would stay here again in a heartbeat."

Reviewed on Nov 14, 2026

River Hotel
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
Book a stay at this business-friendly aparthotel in Chicago. Enjoy a 24-hour fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests ...
9/10 Wonderful! (1,416 reviews)
"Fantastic location and very comfortable apartment style hotel. Grocery store is a few blocks south of the hotel and easily accessible. To the north is the Bean and the fantastic Art Institute of Chicago. Near the historic Hilton Chicago."

Reviewed on Nov 14, 2026

Sentral Michigan Avenue
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4 out of 5
One Superior Place Chicago IL
Stay at this aparthotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
Kasa Magnificent Mile Chicago
Kasa Lake Shore Chicago

Kasa Lake Shore Chicago

4 out of 5
446 East Ontario Street Chicago IL
Stay at this aparthotel in Chicago. Enjoy free WiFi, a rooftop terrace, and parking (surcharge). Popular attractions Michigan Avenue and Chicago Riverwalk are ...
8.8/10 Excellent! (94 reviews)
"It's was very quiet, there a room to study on our floor to get out your room, as well as a terrace to enjoy fresh air. Good location several food spot with walking distance close to Grand Station Chicago trains. We were able to check in and out through the app, receive a code to enter the hotel, ..."

Reviewed on Nov 13, 2026

Kasa Lake Shore Chicago
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.

Stay near popular Southwest Side attractions

Things to do

Cities near Southwest Side

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