Southwest Side Vacations from $618
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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 $957, price is now $618 per person
$618
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,070 reviews)
Wonderful experience, beautiful place. Breakfast on site was a huge plus!
Reviewed on May 13, 2026
The Wade
Downtown Chicago
Price was $1,825, price is now $1,002 per person
$1,002
per person
Jun 17 - Jun 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,825 reviews)
Lovely hotel, very modern and clean. Had fantastic views from the top floor. We were on floor 28 and the skyline was great. Bed very comfortable and it was expected from a 4* hotel. Chicago is a business city, reminded me of a bar man set as its high rised buildings and slightly darker from the shadows of these buildings. Locally there was a few cafes and coffee shops for easy reach for breakfast
Reviewed on May 11, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $963, price is now $624 per person
$624
per person
Jun 22 - Jun 25
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (472 reviews)
Love the amenities. Great location too
Reviewed on May 3, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $968, price is now $639 per person
$639
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
If you plan on staying in this hotel by all means the view is great, but if you plan on moving your vehicle at all the hotel does not validate In-N-Out parking. You have to pay every time you want to leave and come back. Unlike the normal hotel, La Quinta downtown Chicago validate parking yes it’s $70 but you can drive in and out as many times as you want during your stay. Unlike this hotel.
Reviewed on May 8, 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
Back of the Yards
2 out of top 10 points of interest in this area
While Back of the Yards might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Bridgeport Art Center and Zhou B Art Center.
Discover the most popular places to visit in Southwest Side
Wrigley Field
4.5/5(2,149 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Naval Base Great Lakes
4.5/5(461 reviews)
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.
Navy Pier
4.5/5(4,925 reviews)
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Southwest Side
Skydeck - Willis Tower Admission
$44
per adult
96% of travellers recommend
Southwest Side Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
$132 nightly
The price is $157 total per night from May 25 to May 26
$157 total
May 25 - May 26
Total with taxes and fees
8/10 Very Good! (10,220 reviews)
The bar being open late is nice and the staff are very helpful.
Reviewed on May 12, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
$129 nightly
The price is $153 total per night from May 25 to May 26
$153 total
May 25 - May 26
Total with taxes and fees
9/10 Wonderful! (4,285 reviews)
Valet and bellmen were great as always. Polite and helpful. The staff brought up an extra valet for my kids on the pullout couch. Great setup for family with kids! And the restaurant on the corner has the best coffee. We stay here every time we visit, can’t beat location, price and separate space ...
Reviewed on May 13, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $175 total per night from May 25 to May 26
$175 total
May 25 - May 26
Total with taxes and fees
9.4/10 Exceptional! (4,131 reviews)
Wonderful experience, beautiful place. Breakfast on site was a huge plus!
Reviewed on May 13, 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.
