Southwest Side Vacations from $236
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The Latest Southwest Side vacation packages
Price found within the past 48 hours. Click for updated prices.
Wyndham Garden Schaumburg Chicago Northwest
Save 100% on your flight
Price was $361, price is now $236 per person
$236
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
6.6/10 (1,011 reviews)
Nice staff, no breakfast, pool closed and covered, only 2 towels, slow drains .. just expected better from the WYN
Reviewed on Aug 31, 2025
Palmer House a Hilton Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,021, price is now $584 per person
$584
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,890 reviews)
I really like this hotel overall, but 2 of the last 3 times I was here my room wasn’t ready until hours (up to 5) after check-in.
I’ve also had issues with things like the bathtub not draining. Not deal breakers, but kind of annoying.
Reviewed on Aug 30, 2025
Hilton Chicago
Downtown Chicago
Save 100% on your flight
Price was $836, price is now $506 per person
$506
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (2,113 reviews)
Incredibly helpful and personable staff. Comfortable, clean, well kept room.
Reviewed on Aug 31, 2025
Holiday Inn Chicago O'Hare – Rosemont by IHG
O'Hare
Save 100% on your flight
Price was $461, price is now $280 per person
$280
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (2,306 reviews)
An excellent value! Clean and comfortable. Easy airport transport.
Reviewed on Aug 30, 2025
Hyatt Centric Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,089, price is now $667 per person
$667
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,028 reviews)
Overall is good but 1 concern we encountered is there is a clicking sound in our room or near our room, that distracts my husband while sleeping.
Reviewed on Aug 24, 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
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
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
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
$41
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
$162 nightly
The price is $190 total per night from Sep 4 to Sep 5
$190 total
Sep 4 - Sep 5
Total with taxes and fees
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
$168 nightly
The price is $198 total per night from Sep 3 to Sep 4
$198 total
Sep 3 - Sep 4
Total with taxes and fees
8.4/10 Very Good! (4,802 reviews)
"Very nice,everything is around.Highly recommend."
Reviewed on Aug 27, 2025
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
8.2/10 Very Good! (1,156 reviews)
"I enjoyed the location"
Reviewed on Aug 29, 2025
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.