
Southwest Side Holidays
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Top Flight + Hotel Deals in Southwest Side
Price found within the past 48 hours. Click for updated prices.

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was €834, price is now €694 per person
€694
per person
19 Feb - 23 Feb
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
I thoroughly enjoyed this hotel. Many stylish and thoughtful touches. The housekeeping staff did a great job. I stayed 7 nights and could’ve easily stayed 7 more.
Reviewed on 13 Jan 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Price was €1,103, price is now €744 per person
€744
per person
19 Feb - 23 Feb
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Cleanliness, exceptional customer service, and a complimentary upgrade made our stay outstanding! The way the buffet staff efficiently managed the line, guided guests to tables, and consistently kept the food fresh—all while wearing genuine smiles—was truly impressive. Our room was spotless, modern, and well-stocked, exceeding our expectations. We will definitely be back!
Reviewed on 11 Jan 2026



Fairmont Chicago at Millennium Park
Downtown Chicago
Price was €872, price is now €736 per person
€736
per person
19 Feb - 23 Feb
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
Clean room, amazinggggg views, everyone was so nice. Must go downstairs to Toro and get a martini from John!!
Reviewed on 10 Jan 2026
Where 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 there might not be top attractions in Back of the Yards, you can explore the larger area and discover places like Bridgeport Art Center and Zhou B Art Center.
Top hotels in Southwest Side

Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is €165 per night from 20 Jan to 21 Jan
€165
20 Jan - 21 Jan
includes taxes & fees
8.4/10 Very Good! (2,523 reviews)
Yes great Hotel everything was perfect
Reviewed on 12 Jan 2026

Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is €90 per night from 25 Jan to 26 Jan
€90
25 Jan - 26 Jan
includes taxes & fees
8.8/10 Excellent! (3,672 reviews)
Room and hotel overall very clean. Noted some things that could be updated in bathroom(stopper in sink didnt go all the way down, peeling caulk and some missing grout). Minor updates. Our sink was clogged when we checked in and I called the front desk, housekeeping and the hotel hotline 4 different ...
Reviewed on 7 Jan 2026

Club Quarters Hotel Wacker at Michigan, Chicago
75 E Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is €82 per night from 26 Jan to 27 Jan
€82
26 Jan - 27 Jan
includes taxes & fees
8.6/10 Excellent! (2,059 reviews)
Good.
Reviewed on 13 Jan 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.
Popular places to visit

Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Michigan Avenue
You can find the perfect gifts to bring home 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
€38
per adult
98% of travellers recommend

Chicago: Navy Pier Centennial Wheel Ticket
€21
per adult
88% of travellers recommend
Frequently asked questions
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- Aon Center
- Art Institute of Chicago
- Berwyn Holidays
- Buckingham Fountain
- Canalport Riverwalk Park
- Chicago Board of Trade Building
- Visit Canaryville
- Visit Grand Boulevard
- Visit Lower West Side
- Chicago Museum Campus Holidays
- Chicago Place Mall
- Visit South Commons
- Visit Washington Park
- Chicago Holidays
- Cloud Gate
- Credit Union 1 Arena
- Daley Plaza
- Garfield Park Conservatory
- Grant Park
- Hometown Holidays
- Hyde Park Hair Salon
- Hyde Park Holidays
- Lake Meadows Park
- Michigan Avenue
- Millennium Park
- Navy Pier
- Newberry Library
- Visit Oak Lawn
- Oak Park Holidays
- Robie House
- Second Franklin Building
- Smith Museum of Stained Glass Windows
- University of Illinois Chicago
- Water Tower Place
- Willis Tower
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.


