Book Hotels in Southwest Side, IL
Cabins, apartments, houseboats! We offer comfortable & private vacation rentals
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Check prices for these dates
Top Southwest Side hotels
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
$146 nightly
The price is $172 total per night from Apr 28 to Apr 29
$172 total
Apr 28 - Apr 29
Total with taxes and fees
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant ...
Black fast is great
Reviewed on Apr 6, 2026
Hyatt Regency Chicago
151 East Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
$279 nightly
The price is $328 total per night from Apr 7 to Apr 8
$328 total
Apr 7 - Apr 8
Total with taxes and fees
This smoke-free hotel's 4 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center, ...
This hotel is great! Great location, great staff.
Reviewed on Apr 3, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $140 total per night from Apr 26 to Apr 27
$140 total
Apr 26 - Apr 27
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Express ...
Clean room and business friendly
Reviewed on Apr 6, 2026
Swissotel - Chicago
323 E Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
$245 nightly
The price is $288 total per night from Apr 10 to Apr 11
$288 total
Apr 10 - Apr 11
Total with taxes and fees
This hotel features 2 bars/lounges and a 24-hour gym. Traveling on business? Take advantage of the business center, express check-in, and valet parking. A restaurant, ...
Bar menu was not great and overpriced.
Reviewed on Apr 5, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $163 total per night from Apr 26 to Apr 27
$163 total
Apr 26 - Apr 27
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and free full breakfast each morning. Valet parking, a business center, and ...
The room was very clean but the amenities are quite dirty. In general is a big hotel with a lot of movement, many families and a lot of people everywhere, so the breakfast (which is great by the way) is very busy.
Reviewed on Apr 6, 2026
Aloft Chicago Mag Mile
243 E. Ontario Chicago IL
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $124 total per night from Apr 12 to Apr 13
$124 total
Apr 12 - Apr 13
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and perks like free WiFi. Valet parking, a business center, and a snack bar/deli ...
Room was dirty and unstocked with bath towels and was clothes.
Reviewed on Apr 5, 2026
The Wade
644 N Lake Shore Dr Chicago IL
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $151 total per night from Apr 7 to Apr 8
$151 total
Apr 7 - Apr 8
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public ...
The staff were friendly. The bed sheets are weird not having a fitted sheet on them. The service/wifi connection sucks but doesn’t matter when you’re busy enjoying the city! Just weirded out about the sheets
Reviewed on Apr 6, 2026
Hotel Felix River North/Magnificent Mile
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $147 total per night from Apr 7 to Apr 8
$147 total
Apr 7 - Apr 8
Total with taxes and fees
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet ...
Great experience and friendly staff
Reviewed on Apr 6, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $129 total per night from Apr 16 to Apr 17
$129 total
Apr 16 - Apr 17
Total with taxes and fees
This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center ...
Air conditioner was really noisy, they told me there is a free parking when i booked, no towel in the bathroom
Reviewed on Apr 6, 2026
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.
Hotels in Southwest Side with star-rating
Check Southwest Side Hotels by Star Rating
5 Star Hotels
10 properties
Recent Southwest Side hotel reviews by fellow wanderers
Congress Plaza Hotel
1 out of 5
Posted 1 hour ago
Travelocity Verified Review
"Air conditioner was really noisy, they told me there is a free parking when i booked, no towel in the bathroom "
A verified traveler stayed at Congress Plaza Hotel
Explore More Ways to Travel with Travelocity
- Guest Houses in Ashland-63rd Station
- Hotels near Ashland-63rd Station
- Hotels near Canalport Riverwalk Park
- Garfield Ridge Hotels
- Hotels near Marquette Park
- Apartments in 35th-Archer Station
- 4 Star Hotels in Ducktown
- Ducktown Hotels
- Armour Square Hotels
- Hotels near Midway Intl.
- West Englewood Hotels
- Hotels near Rate Field
- Motels in Kedzie Station
- Fuller Park Hotels
- 3 Star Hotels in Gage Park
- Gage Park Hotels
- Hotels near Zhou B Art Center
- Chicago Lawn Hotels
- West Elsdon Hotels
- Glendale Hotels
- Mckinley Park Hotels
- Condos in Garfield Station
- Hotels with Hot Tubs in Chicago
- Chicago Hotels
- Lower West Side Hotels
- Washington Park Hotels
- Hotels near Bridgeport Art Center
- Apartments in Midway Station
- Sleepy Hollow Hotels
- 3 Star Hotels in Canaryville
- Canaryville Hotels
- Little Village Hotels
- 5 Star Hotels in Corwith
- Arcade Hotels in Archer Heights
- Cheap Hotels in Archer Heights
- Hotels with Shopping in Archer Heights
- Archer Heights Hotels
- Bridgeport Hotels
- Downtown Chicago Hotels
- West Lawn Hotels
- Brighton Park Hotels
- Pet Friendly Hotels in Englewood
- Romantic Getaways & Hotels in Englewood
- Englewood Hotels
- Heart of Chicago Hotels
- Flights from Midway Intl.
- Delta Hartford (BDL) to Chicago (MDW) flights
- Delta Cincinnati (CVG) to Chicago (MDW) flights
- Delta Detroit (DTW) to Chicago (MDW) flights
- Delta Atlanta (ATL) to Chicago (MDW) flights
- Delta Minneapolis (MSP) to Chicago (MDW) flights
- Delta San Jose (SJC) to Chicago (MDW) flights
- Delta Washington (DCA) to Chicago (MDW) flights
- Volaris Durango (DGO) to Chicago (MDW) flights
- Flights from Atlanta (ATL) to Chicago (MDW)
- Flights from Austin (AUS) to Chicago (MDW)
- Flights from Nashville (BNA) to Chicago (MDW)
- Flights from Boston (BOS) to Chicago (MDW)
- Flights from Baltimore (BWI) to Chicago (MDW)
- Flights from Charlotte (CLT) to Chicago (MDW)
- Flights from Columbus (CMH) to Chicago (MDW)
- Flights from Denver (DEN) to Chicago (MDW)
- Flights from Dallas (DFW) to Chicago (MDW)
- Flights from Detroit (DTW) to Chicago (MDW)
- Flights from Newark Liberty Intl. Airport (EWR) to Chicago (MDW)
- Flights from Fort Lauderdale (FLL) to Chicago (MDW)
- Flights from Houston (IAH) to Chicago (MDW)
- Flights from Jacksonville (JAX) to Chicago (MDW)
- Flights from New York (JFK) to Chicago (MDW)
- Flights from Las Vegas (LAS) to Chicago (MDW)
- Flights from Los Angeles (LAX) to Chicago (MDW)
- Flights from New York (LGA) to Chicago (MDW)
- Flights from Kansas City (MCI) to Chicago (MDW)
- Flights from Orlando (MCO) to Chicago (MDW)
- Flights from Miami (MIA) to Chicago (MDW)
- Flights from Minneapolis (MSP) to Chicago (MDW)
- Flights from New Orleans (MSY) to Chicago (MDW)
- Flights from Oakland (OAK) to Chicago (MDW)
- Flights from Ontario (ONT) to Chicago (MDW)
- Flights from Portland (PDX) to Chicago (MDW)
- Flights from Philadelphia (PHL) to Chicago (MDW)
- Flights from Phoenix (PHX) to Chicago (MDW)
- Flights from Pittsburgh (PIT) to Chicago (MDW)
- Flights from Raleigh (RDU) to Chicago (MDW)
- Flights from Fort Myers (RSW) to Chicago (MDW)
- Flights from San Diego (SAN) to Chicago (MDW)
- Flights from San Francisco (SFO) to Chicago (MDW)
- Flights from Salt Lake City (SLC) to Chicago (MDW)
- Flights from Orange County (SNA) to Chicago (MDW)
- Flights from St. Louis (STL) to Chicago (MDW)
- Flights from Tampa (TPA) to Chicago (MDW)
- Flights to Chicago
- Hotels near United Center
- Car rentals at Chicago Airport (MDW)
- Cheap Hotels in Chicago
- Hotels near Grant Park
- Flights to Chicago
- Hotels near Chicago Riverwalk
- Hotels near Soldier Field
- Hotels in Chicago
- Car rentals in Chicago
- Hotels near McCormick Place
- Hotels in Hyde Park
- Hotels in Downtown Chicago
