Southwest Side Vacations from $572
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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 $839, price is now $572 per person
$572
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)
Excellent spot, in the perfect location. Parking at the property is pretty expensive, but there are cheaper parking garages close by.
Reviewed on Jul 6, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,232, price is now $831 per person
$831
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)
The hotel was on the pier and
Reviewed on Jul 7, 2026
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,118, price is now $773 per person
$773
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,136 reviews)
Great location can get a bit noisy but really nice hotel.
Reviewed on Jul 8, 2026
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
Price was $1,221, price is now $864 per person
$864
per person
Aug 26 - Aug 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
There is a family lounge and pool and it was really helpful for us. (we have 2 kids bc7&4 yo)
The spacious room with full kitchen is very comfortable as well.
We have 2 negative points. One is location. It is located around River North but a little bit far from the busy area. So there are not so many places to eat around. Another one is the water pressure in the shower is very weak.
Reviewed on Jul 7, 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
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$197 nightly
The price is $234 total per night from Jul 9 to Jul 10
$234 total
Jul 9 - Jul 10
Total with taxes and fees
9.2/10 Wonderful! (1,874 reviews)
"Convenient location and friendly staff."
Reviewed on Jul 7, 2026
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! (1,711 reviews)
"They had extra charges, when checking in to my room. Also, the couch had stains in my room and only one of us could take a shower. The shower was plugged and filled up with water. Would not drain."
Reviewed on Jul 8, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$181 nightly
The price is $215 total per night from Jul 9 to Jul 10
$215 total
Jul 9 - Jul 10
Total with taxes and fees
8/10 Very Good! (10,200 reviews)
"Dated hotel but the rooms are kept clean, updated flooring and really nice bedding. Fantastic location downtown, less than a mile walking distance from Museum Campus."
Reviewed on Jul 7, 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.
