Southwest Side Vacations from $331
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The Latest Southwest Side vacation packages
Price found within the past 48 hours. Click for updated prices.
Hampton Inn Chicago-Carol Stream
Save 100% on your flight
Price was $523, price is now $331 per person
$331
per person
Oct 8 - Oct 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (1,008 reviews)
The room was very clean. The customer service was great and the bed was very comfortable
Reviewed on Sep 2, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $2,110, price is now $1,258 per person
$1,258
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
Best, very clean, best view, really enjoyed the stay!
Reviewed on Sep 2, 2025
Hilton Chicago/Oak Lawn
Save 100% on your flight
Price was $809, price is now $513 per person
$513
per person
Oct 8 - Oct 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (1,022 reviews)
easy to get to and shopping and eating options in the aera
Reviewed on Sep 2, 2025
Don't see what you're looking for?
See all available trips from Columbus to Southwest Side
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
Back of the Yards
2 out of top 10 points of interest in this area
While Back of the Yards might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Bridgeport Art Center and Zhou B Art Center.
Discover the most popular places to visit in Southwest Side
Wrigley Field
4.5/5(2,128 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
4.5/5(332 reviews)
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Navy Pier
4.5/5(4,870 reviews)
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Southwest Side
Wendella's 90-min Chicago River Architecture Tour
$45
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
$45
per adult
96% of travellers recommend
Southwest Side Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$170 nightly
The price is $200 total per night from Sep 4 to Sep 5
$200 total
Sep 4 - Sep 5
Total with taxes and fees
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
$183 nightly
The price is $215 total per night from Sep 22 to Sep 23
$215 total
Sep 22 - Sep 23
Total with taxes and fees
The Wade
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
$167 nightly
The price is $196 total per night from Sep 22 to Sep 23
$196 total
Sep 22 - Sep 23
Total with taxes and fees
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.
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- Stephen A. Douglas Tomb and Memorial
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- Visit South Englewood
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- Enterprise Rental Cars in Midway Intl.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.