Southwest Side Vacations from $309
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The Latest Southwest Side vacation packages
Price found within the past 48 hours. Click for updated prices.
Palmer House a Hilton Hotel
Downtown Chicago
Save 100% on your flight
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,773 reviews)
Beautiful historic hotel! Loved the live music in the lobby. I was there in a traditional room sith 2 double beds, and then i upgraded to a suite. Both were nice rooms, but i LOVE a good suite!
Personnel at the hotel were kind and helpful.
Have a cocktail and a brownie in the lobby- you won't regret it!
Reviewed on Jul 15, 2025
The French Country Inn Lake Geneva
Save 100% on your flight
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.8/10 Excellent! (126 reviews)
The views are great in this historic Inn. Layed back but still classy. Away from the crowds but great dining that adds some fun. Could use a few room convinces and amenities like a working coffee and micro.
Reviewed on Jun 29, 2025
The Peninsula Chicago
Downtown Chicago
Save 100% on your flight
per person
Sep 15 - Sep 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Everything about this hotel is on point. The staff is professional and gracious. The property is extremely well maintained. They leave no detail of your comfort unaddressed.
Reviewed on Jul 15, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
Hotel is beautiful! Staff was amazing! It was super clean, and the buffet was to die for! However, the wifi did not work! I needed it to do work on my computer and I couldn’t do anything!
Reviewed on Jul 14, 2025
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
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(2,128 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Navy Pier
4.5/5(4,870 reviews)
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Michigan Avenue
4.5/5(332 reviews)
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
What to do in Southwest Side
Wendella's 90-min Chicago River Architecture Tour
$45
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
$45
per adult
94% of travellers recommend
Southwest Side Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$174 nightly
The price is $205 total per night from Aug 7 to Aug 8
$205 total
Aug 7 - Aug 8
Total includes taxes and fees
7.8/10 Good! (8,972 reviews)
"The area was pretty nice, and hotel was remodeled in some areas. Didnt like the bathroom was dirty the bucket wasnt empty when we arrived"
Reviewed on Jul 15, 2025
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave, Chicago, IL
Fully refundable
$251 nightly
The price is $289 total per night from Aug 7 to Aug 8
$289 total
Aug 7 - Aug 8
Total includes taxes and fees
9/10 Wonderful! (2,047 reviews)
"Great. Just hard to get parked to get into hotel due to busy location."
Reviewed on Jul 15, 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $172 total per night from Aug 10 to Aug 11
$172 total
Aug 10 - Aug 11
Total includes taxes and fees
8.8/10 Excellent! (2,445 reviews)
"Good"
Reviewed on Jul 15, 2025
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.