Southwest Side Vacations from $791
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The Latest Southwest Side vacation packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,301, price is now $791 per person
$791
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,586 reviews)
Awesome location for boat/beach/dining!
Reviewed on Jul 5, 2026
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,417, price is now $926 per person
$926
per person
Aug 26 - Aug 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
We had a great stay at Level. I think it’s a really good option for a longer trip, especially if you want more of an apartment-style setup and a convenient location. The staff was amazing from start to finish and truly made the stay stand out. Everyone was kind, helpful, and welcoming, and the service alone would make me come back.
The location is also very convenient and worked well for getting around Chicago, especially if you don’t mind doing a bit of walking. For our family, I think it felt a little more geared toward professionals or longer stays than a traditional family hotel, but overall we had a very positive experience. If you’re staying in Chicago for more than a couple of nights and want something comfortable and convenient, I would definitely recommend it.
Reviewed on Jul 2, 2026
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
Price was $1,226, price is now $805 per person
$805
per person
Sep 23 - Sep 27
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
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,284, price is now $846 per person
$846
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well
Reviewed on Jun 26, 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
$163 nightly
The price is $193 total per night from Jul 27 to Jul 28
$193 total
Jul 27 - Jul 28
Total with taxes and fees
8.2/10 Very Good! (1,694 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
$192 nightly
The price is $229 total per night from Jul 8 to Jul 9
$229 total
Jul 8 - Jul 9
Total with taxes and fees
8/10 Very Good! (10,173 reviews)
"No parking spot as mention, you need to find a public parking spot and pay extra $40 for 24h"
Reviewed on Jul 5, 2026
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$181 nightly
The price is $215 total per night from Jul 7 to Jul 8
$215 total
Jul 7 - Jul 8
Total with taxes and fees
9.2/10 Wonderful! (1,855 reviews)
"Great hotel and location."
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.
