Southwest Side Vacations from $522
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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 $779, price is now $522 per person
$522
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,797 reviews)
Loved this hotel and their customer service. Overall, a great experience, highly recommend.
Reviewed on Jul 4, 2026
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 $1,040, price is now $686 per person
$686
per person
Aug 28 - 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 $1,343, price is now $925 per person
$925
per person
Sep 4 - Sep 7
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
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,422, price is now $980 per person
$980
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,764 reviews)
We generally stay here when we travel to Chicago by the quality of service has diminished lately. Additionally if your booking is through Expedia, everything gets complicated and not well treated.
Reviewed on Jul 5, 2026
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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
$172 nightly
The price is $204 total per night from Jul 6 to Jul 7
$204 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
$121 nightly
The price is $144 total per night from Jul 6 to Jul 7
$144 total
Jul 6 - Jul 7
Total with taxes and fees
8/10 Very Good! (10,158 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
$174 nightly
The price is $207 total per night from Jul 8 to Jul 9
$207 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
