Southwest Side Vacations from $203
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The Latest Southwest Side vacation packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Prospect Heights by IHG
Save 100% on your flight
Price was $344, price is now $203 per person
$203
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9/10 Wonderful! (851 reviews)
Clan quiet room. Comfortable bed. Great staff. Need to upgrade the fitness center
Reviewed on Nov 11, 2025
Sand Hill On The Lake
Price was $500, price is now $284 per person
$284
per person
Dec 31 - Jan 3
found 2 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.8/10 Excellent! (77 reviews)
The view on the lake is beautiful and the fireplace made it so cozy during our fall visitl
Reviewed on Nov 10, 2025
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $346, price is now $209 per person
$209
per person
Jan 23 - Jan 25
found 16 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
A great location, a fabulous building, and a delightful room. The one mystery was a background thumping noise that persisted throughout the stay. Fortunately, didn't disturb sleep. The reception staff sloughed off any knowledge or interest in the cause, but we couldn't imagine that the source was an unknown to hotel staff, and potentially fixable.
Reviewed on Nov 12, 2025
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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 SeatGeek Stadium and Chicago Ridge Shopping Mall while you're in the area.
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.
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.
Navy Pier
4.5/5(4,870 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
98% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
84% of travellers recommend
Southwest Side Hotel Deals
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $112 total per night from Nov 25 to Nov 26
$112 total
Nov 25 - Nov 26
Total with taxes and fees
8.4/10 Very Good! (5,235 reviews)
Clean room; kind and courteous staff; excellent breakfast and happy hour included
Reviewed on Nov 10, 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $115 total per night from Dec 7 to Dec 8
$115 total
Dec 7 - Dec 8
Total with taxes and fees
8.8/10 Excellent! (3,280 reviews)
Room was clean, bell staff and front desk were very helpful and accommodating. The restaurant staff were very friendly and accommodating!
Reviewed on Nov 13, 2025
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $136 total per night from Nov 16 to Nov 17
$136 total
Nov 16 - Nov 17
Total with taxes and fees
8/10 Very Good! (9,545 reviews)
Totally fantastic stay! Staff fantastic!
Reviewed on Nov 13, 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.
