Southwest Side Vacations from $427
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The Latest Southwest Side vacation packages
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
Downtown Chicago
Save 100% on your flight
Price was $632, price is now $427 per person
$427
per person
Jul 1 - Jul 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (2,574 reviews)
Great hotel in the perfect location. The staff was super friendly. We would definitely stay here again.
Reviewed on May 12, 2026
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,830, price is now $1,006 per person
$1,006
per person
Jun 18 - Jun 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
This property has a great location. The hotel was really clean! We enjoyed the bar atmosphere, and we had a delicious appetizer! I will highly recommend this location for a great getaway for couples! Page at the front desk and Prudencia in housekeeping were amazing!
Reviewed on May 13, 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 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (472 reviews)
Really nice building with top-notch amenities in a fabulous location. Room was large, clean and well equipped with high end appliances, walk-in closet, floor to ceiling windows with lots of light. Overall, a great experience. Would stay again.
Reviewed on May 12, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $961, price is now $629 per person
$629
per person
Jul 1 - Jul 4
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
Eurostars Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,515, price is now $1,015 per person
$1,015
per person
Jun 18 - Jun 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,506 reviews)
Needs to be updated nice views though
Reviewed on May 13, 2026
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(2,149 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
$135 nightly
The price is $161 total per night from May 25 to May 26
$161 total
May 25 - May 26
Total with taxes and fees
8/10 Very Good! (10,223 reviews)
The lakeview was spectacular and the rooms had ample space.
Reviewed on May 13, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
$130 nightly
The price is $155 total per night from May 25 to May 26
$155 total
May 25 - May 26
Total with taxes and fees
9/10 Wonderful! (4,289 reviews)
Had a great stay! The hotel was clean, comfortable, and the staff was very friendly. The location was perfect, close to everything we wanted to do, with lots of restaurants, shopping, and attractions nearby. It made getting around super easy.
Reviewed on May 13, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
$150 nightly
The price is $179 total per night from May 25 to May 26
$179 total
May 25 - May 26
Total with taxes and fees
9.4/10 Exceptional! (4,135 reviews)
The property, our room, and the staff were all FIVE STARS! Highly recommend this place!!
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.
