Southwest Side

Travel Guide

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.
An indoor exhibit with a large informational display about the Battle of Midway Memorial.
Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
7353 S Cicero Avenue Chicago IL
The price is P8,956 per night from Oct 25 to Oct 26
P8,956
P11,140 total
Oct 25 - Oct 26
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
Holiday Inn Chicago – Midway Airport S by IHG
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is P10,155 per night from Sep 27 to Sep 28
P10,155
P12,073 total
Sep 27 - Sep 28
includes taxes & 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! (5,435 reviews)
"Elevator was broken, took 15 minutes each time I needed it"

Reviewed on Sep 24, 2026

River Hotel
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is P10,115 per night from Oct 25 to Oct 26
P10,115
P12,026 total
Oct 25 - Oct 26
includes taxes & 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! (10,201 reviews)
"Not well thought or planned for the convenience of the traveler. For example there was way to control the room temperature, sheets were short for tall people"

Reviewed on Sep 24, 2026

Congress Plaza Hotel
See all 4,941 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
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 ...
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 ...
9.4/10 Exceptional! (923 reviews)
"Perfect for our needs"

Reviewed on Sep 23, 2026

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 ...
Kasa Lake Shore Chicago
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.

Stay near popular Southwest Side attractions

Marquette Park

9.4/10 (3 reviews)
After visiting Marquette Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art scene.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

P1,685
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

P2,496
per adult
92% of travellers recommend
Art Institute of Chicago
Flyover in Chicago

Flyover in Chicago

P1,744
per adult
98% of travellers recommend
Flyover in Chicago
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

P1,535
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

P2,647
per adult
90% of travellers recommend
Skydeck Chicago at Willis Tower
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

P2,527
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Southwest Side