Southwest Side Vacations from $460
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The Latest Southwest Side vacation packages
Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Save 100% on your flight
Price was $824, price is now $460 per person
$460
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,975 reviews)
The restrooms do not have built in ventilation and the hotel needs to be updated overall.
Reviewed on Aug 25, 2025
The Emily Hotel
Downtown Chicago
Price was $1,339, price is now $675 per person
$675
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend.
Also the coffee bags ? PERFECTION. Just had to add that
Reviewed on Aug 22, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $1,291, price is now $661 per person
$661
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,342 reviews)
Liked everything. Appreciated later check out time.
Front desk very helpful. Breakfast was⭐️🌟🥇
Reviewed on Aug 29, 2025
Level Chicago – Old Town
Downtown Chicago
Price was $1,001, price is now $520 per person
$520
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.
Reviewed on Aug 27, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was $2,080, price is now $1,111 per person
$1,111
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
5 star hotel that goes above and beyond. My family loved staying at the Trump
Reviewed on Aug 29, 2025
Don't see what you're looking for?
See all available trips from Singapore 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
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
$45
per adult
96% of travellers recommend
Southwest Side Hotel Deals
The Wade
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $177 total per night from Sep 4 to Sep 5
$177 total
Sep 4 - Sep 5
Total with taxes and fees
8.2/10 Very Good! (1,156 reviews)
"I enjoyed the location"
Reviewed on Aug 29, 2025
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$170 nightly
The price is $200 total per night from Sep 1 to Sep 2
$200 total
Sep 1 - Sep 2
Total with taxes and fees
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
$168 nightly
The price is $198 total per night from Sep 3 to Sep 4
$198 total
Sep 3 - Sep 4
Total with taxes and fees
8.4/10 Very Good! (4,802 reviews)
"Very nice,everything is around.Highly recommend."
Reviewed on Aug 27, 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.
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- Chicago Vacations
- Visit Gage Park
- Visit New City
- Visit Garfield Manor
- Visit Brighton Park
- Visit Chicago Lawn
- Visit West Elsdon
- Visit West Englewood
- Visit Englewood
- Visit Ducktown
- Bridgeport Art Center
- Zhou B Art Center
- Visit Canaryville
- South Englewood Vacations
- Visit Archer Heights
- Visit Corwith
- Visit McKinley Park
- Stephen A. Douglas Tomb and Memorial
- Visit West Lawn
- Visit South Englewood
- Car rentals near Chicago
- Car rental Chicago Airport (MDW)
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- Enterprise Rental Cars in Midway Intl.
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- Dollar Rent A Car Rental Cars in Midway Intl.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.