Southwest Side Vacations from $744
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The Latest Southwest Side vacation packages
Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
Price was $1,141, price is now $744 per person
$744
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,013 reviews)
This location is ideal for families. The amenities provided are exceptional, scoring a perfect ten out of ten. It offers ample space for a family, including two bathrooms, which was greatly appreciated by my children. The property is well-equipped to ensure a comfortable stay. My only reservation pertains to its distance from Michigan Avenue and the Riverwalk, necessitating a vehicle to access these popular destinations. Otherwise, the experience was flawless.
Reviewed on Jul 2, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,699, price is now $1,038 per person
$1,038
per person
Aug 26 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,586 reviews)
Excellent customer service, amazing staff!
Reviewed on Jul 4, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $2,194, price is now $1,429 per person
$1,429
per person
Aug 26 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
Me encantó volveria mil veces a ese hotel
Reviewed on Jul 4, 2026
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View all tripsWhere to stay in Southwest Side
Find the best Southwest Side areas and neighborhoods for the activities you enjoy most. Learn more about Southwest Side
Clearing
4/5(72 area reviews)
You'll appreciate the restaurants during your time in Clearing and you might want to plan a stop by Wintrust Sports Complex and SeatGeek Stadium while you're in the area.
Stay near popular Southwest Side attractions
What to do in Southwest Side
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
Southwest Side Hotel Deals
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$134 nightly
The price is $159 total per night from Jul 6 to Jul 7
$159 total
Jul 6 - Jul 7
Total with taxes and fees
8.2/10 Very Good! (1,689 reviews)
"We like our room, very clean and spacious"
Reviewed on Jul 4, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $141 total per night from Jul 8 to Jul 9
$141 total
Jul 8 - Jul 9
Total with taxes and fees
8/10 Very Good! (10,157 reviews)
"Great location- good price for a holiday weekend"
Reviewed on Jul 4, 2026
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$172 nightly
The price is $204 total per night from Jul 8 to Jul 9
$204 total
Jul 8 - Jul 9
Total with taxes and fees
9.2/10 Wonderful! (1,846 reviews)
"Great staff"
Reviewed on Jul 5, 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.
Find the Best Southwest Side Vacation Packages
Southwest Side Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
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- Michigan Avenue
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- Chicago Cultural Center
- Lincoln Park Zoo
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- Roosevelt University
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- Columbia College Chicago
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- Robert W Roloson Houses
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- Depaul University-Loop Campus
- South Loop Vacations
- Chicago Museum Campus Vacations
- Gen. John Logan Memorial
- 311 S Wacker Dr
- Maggie Daley Park
- Goodman Theater
- Ping Tom Memorial Park
- Daley Plaza
- Civic Opera House
- Hyde Park Vacations
- Anna and Frederick Douglass Park
- Navy Pier
- Chicago Symphony Orchestra
- United Center
- Ohio Street Beach
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- Maxwell Street Market
- Cibc Theatre
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- Shops at North Bridge
- Jane Addams' Hull-House Museum
- Mccormick Tribune Center
- Willis Tower
- Grace Abbott Homes Vacations
- Lakefront Trail
- Canalport Riverwalk Park
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- Rookery
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- Downtown Chicago Vacations
- Cna Center
- Sr Crown Hall
- Skydeck Ledge
- West Loop Vacations
- Merchandise Mart
- University of Illinois Chicago
- Harold Washington Library Center
- Tribune Tower
- St. John Cantius Church
- Chicago Children's Museum
- Bridgeport Art Center
- Burnham Park
- Chinatown Vacations
- Art Institute of Chicago
- Garfield Park
- Water Tower Place
- St. Basil Greek Orthodox Church
- Marshall Field Building
- 333 West Wacker Drive
- Lincoln Park Conservatory
- Robie House
- Driehaus Museum
- Chicago Vacations
- Zhou B Art Center
- Chicago Riverwalk
- Grant Park
- Auditorium Building and Theatre
- Richard J. Daley Center
- Marina City
- Illinois Institute of Technology
- Magnificent Mile Vacations
- Wrigley Field
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- Michigan Avenue Bridge
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- Carbide and Carbon Building
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- The Salt Shed
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- Chicago Board of Trade Building
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.