Southwest Side Vacations from $555
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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 $842, price is now $555 per person
$555
per person
Sep 24 - Sep 27
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,809 reviews)
The staff did not explain that room cleaning was available only upon request. For the breakfast specialty coffee you had to wait for the front desk staff to be available.
Reviewed on Jul 6, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,055, price is now $679 per person
$679
per person
Sep 24 - Sep 27
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,586 reviews)
The property was amazing including the buffet breakfast.
Reviewed on Jul 6, 2026
Omni Chicago Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,169, price is now $761 per person
$761
per person
Sep 24 - Sep 27
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
This was a very clean and nice hotel. I enjoyed the room.
Reviewed on Jul 6, 2026
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,635, price is now $1,079 per person
$1,079
per person
Aug 5 - Aug 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,323 reviews)
Great boutique hotel in a great location! Definitely will stay here again when visiting Chicago.
Reviewed on Jul 5, 2026
The Talbott, Autograph Collection
Downtown Chicago
Save 100% on your flight
Price was $1,245, price is now $837 per person
$837
per person
Aug 6 - Aug 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (128 reviews)
A hidden gem in the heart of the Gold Coast! Wonderful staff! Shout out to Steve! He made us feel right at home! Coffee machines in the room were amazing, the coffee was delicious! Thank you to all the staff for all that they do! Til next time!
Reviewed on Jul 5, 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
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $171 total per night from Jul 7 to Jul 8
$171 total
Jul 7 - Jul 8
Total with taxes and fees
8.2/10 Very Good! (1,696 reviews)
"Tried to use the very small hair dryer only to find out it quite in a puff of black smoke and smelled up the whole room."
Reviewed on Jul 5, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$138 nightly
The price is $164 total per night from Jul 7 to Jul 8
$164 total
Jul 7 - Jul 8
Total with taxes and fees
8/10 Very Good! (10,181 reviews)
"The fire alarm system starts beeping at the middle of the night and no one to replace the battery. The bath tap was rusty. No microwave."
Reviewed on Jul 6, 2026
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$170 nightly
The price is $203 total per night from Jul 8 to Jul 9
$203 total
Jul 8 - Jul 9
Total with taxes and fees
9.2/10 Wonderful! (1,857 reviews)
"This was a very clean and nice hotel. I enjoyed the room."
Reviewed on Jul 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.
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.
