
Southwest Side Vacations from $331
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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 $576, price is now $331 per person
$331
per person
Mar 28 - Mar 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Continental breakfast was great. Rooms were immaculate and staff were professional and friendly.
Reviewed on Jan 14, 2026



Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $632, price is now $390 per person
$390
per person
Mar 28 - Mar 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
I stayed 5 nights total, 4 nights in a two BR, 1 bath with a balcony and the last night in a one BR. The 2BR was great. It faced East, received a lot of sunlight, was clean, modern and the bed was very comfortable. The gym had what I needed too. actually liked sleeping with the sound of the el nearby because I used to live in the area. I did not give it 5 stars because the walls are super thin. Someone had a party next to me and it was impossible to sleep hearing voices straight through the walls. Being a newer building, I don’t think the best quality appliances or fixtures were chosen. My ice machine wasn’t working and the heat/fan only worked in certain areas in the 2BR. Additional lighting should be added. The 1BR shower fixtures and drain needed some attention. That said, Mihajlo and the front desk staff were very helpful and attentive and helped me with whatever I needed. The 1BR seemed more like a studio to m. I’d prefer to book directly through Level, but it was a better price with Expedia. I still thought it was pricey but I was overall happy with my stay.
Reviewed on Jan 12, 2026

Holiday Inn Chicago – Midway Airport S by IHG
West Lawn
Save 100% on your flight
Price was $564, price is now $348 per person
$348
per person
Apr 3 - Apr 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,000 reviews)
I was greeted with a smile we checking our room and we were late. They were very accommodating. They have a bar which we went over to eat from. I don’t know the bartender’s real name we were cold to call her TT. She was the very best ever very kind very sociable and friendly. I will be returning to this property the next time I’m in Chicago. I really had a great experience at this hotel with the staff is also includes the manager the hotel clerk, as well as the security guard. I will give my experience at this hotel five stars.
Reviewed on Jan 12, 2026
Don't see what you're looking for?
See all available trips from Des Moines 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
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Michigan Avenue
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.

Navy Pier
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
100% of travellers recommend

Chicago Bulls Basketball Game at United Center
$83
per adult
80% of travellers recommend

Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
Southwest Side Hotel Deals

Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $182 total per night from Feb 1 to Feb 2
$182 total
Feb 1 - Feb 2
Total with taxes and fees
8.4/10 Very Good! (2,527 reviews)
THe staff was very efficient and professional and the breakfast was great.
Reviewed on Jan 13, 2026

Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $105 total per night from Jan 25 to Jan 26
$105 total
Jan 25 - Jan 26
Total with taxes and fees
8.8/10 Excellent! (3,706 reviews)
10/10
Reviewed on Jan 14, 2026

Club Quarters Hotel Wacker at Michigan, Chicago
75 E Wacker Dr Chicago IL
$88 nightly
The price is $103 total per night from Jan 30 to Jan 31
$103 total
Jan 30 - Jan 31
Total with taxes and fees
8.6/10 Excellent! (2,062 reviews)
Helpful staff! Great view of the river from our room.
Reviewed on Jan 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.




















