Far Southwest Side Vacations from $413
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The Latest Far 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 2 - Sep 7
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
Virgin Hotels Chicago
Downtown Chicago
Save 100% on your flight
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
The hotel staff were very pleasant, the room was clean, and the hotel was located in a convenient area.
Reviewed on Jul 17, 2025
Arlo Chicago
Downtown Chicago
Save 100% on your flight
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,785 reviews)
The servers and bartenders at the property were amazing! Gentleman who stored our luggage was polite and extremely attentive!
Reviewed on Jul 16, 2025
Don't see what you're looking for?
See all available trips from Columbus to Far Southwest Side
View all tripsWhere to stay in Far Southwest Side
Find the best Far Southwest Side areas and neighborhoods for the activities you enjoy most. Learn more about Far Southwest Side
Ashburn
The restaurants and churches are just a few features travelers like about Ashburn. If you want to do some sightseeing nearby, Chicago Ridge Shopping Mall and Balzekas Museum of Lithuanian Culture are a few top places to visit.
Discover the most popular places to visit in Far 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 Far 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
Far Southwest Side Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$169 nightly
The price is $199 total per night from Aug 10 to Aug 11
$199 total
Aug 10 - Aug 11
Total includes taxes and fees
7.8/10 Good! (8,865 reviews)
"It is a historic place"
Reviewed on Jul 18, 2025
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave, Chicago, IL
Fully refundable
$281 nightly
The price is $324 total per night from Jul 24 to Jul 25
$324 total
Jul 24 - Jul 25
Total includes taxes and fees
9/10 Wonderful! (2,064 reviews)
"Convenient"
Reviewed on Jul 17, 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $170 total per night from Aug 10 to Aug 11
$170 total
Aug 10 - Aug 11
Total includes taxes and fees
8.8/10 Excellent! (2,474 reviews)
"Rocky was awesome and gave us great recommendations. Check in lady was nice and had no issues. Only issue we had was the bar. My husband waiting a good 30 min with no acknowledgment and it wasn’t busy. This happened 2 nights in a row. Someone from the food area noticed he hadn’t been helped and helped ..."
Reviewed on Jul 18, 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 Far Southwest Side Vacation Packages
Far 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.