Southwest Side Vacations from $558
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The Latest Southwest Side vacation packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $836, price is now $558 per person
$558
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,809 reviews)
The room was small, but fine. The bed was comfortable. The TV was too big so it covered the thermostat control panel, and the remote Guide button didn’t work. Also, the water pressure in the shower was super weak… glad I didn’t need to wash my hair.
But location, general vibe, and staff were great.
Reviewed on Jul 8, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,130, price is now $721 per person
$721
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,586 reviews)
Perfect! Fantastic breakfast! Will be returning!
Reviewed on Jul 8, 2026
Omni Chicago Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,039, price is now $682 per person
$682
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
very good experience overall, few concerns:
- didnt like the bar ambience/availability
- inconvenient lobby system - especially for folks checking in later in the night
Reviewed on Jul 8, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,179, price is now $790 per person
$790
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
Great place to stay for a night after exploring all day. I was able to see the city right from the window. Recommend this place for sure
Reviewed on Jul 8, 2026
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
Save 100% on your flight
Price was $863, price is now $579 per person
$579
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (3,939 reviews)
The property was outdated but fine. The room seemed clean.
There was not rest during our stay here. You can hear everything going on outside and every door that opens and closes. There I security guard on the floor that keeps walking around and his radio is so loud, someone is constantly talking on the other side that we could not sleep multiple nights.
It is in the great location but I would recommend paying little extra for some good sleep at night.
Reviewed on Jul 6, 2026
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
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
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$259 nightly
The price is $308 total per night from Jul 26 to Jul 27
$308 total
Jul 26 - Jul 27
Total with taxes and fees
9.2/10 Wonderful! (1,878 reviews)
"very good experience overall, few concerns: - didnt like the bar ambience/availability - inconvenient lobby system - especially for folks checking in later in the night"
Reviewed on Jul 8, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$154 nightly
The price is $183 total per night from Jul 9 to Jul 10
$183 total
Jul 9 - Jul 10
Total with taxes and fees
8.2/10 Very Good! (1,713 reviews)
"Nice place to stay"
Reviewed on Jul 8, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$201 nightly
The price is $239 total per night from Jul 9 to Jul 10
$239 total
Jul 9 - Jul 10
Total with taxes and fees
8/10 Very Good! (10,204 reviews)
"Great location. The building has so much history and yes it is old but they’ve done a nice job in trying to keep it up."
Reviewed on Jul 8, 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
