
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.


Level Chicago – Old Town
Downtown Chicago
Price was €1,692, price is now €1,153 per person
€1,153
per person
29 Dec - 4 Jan
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Everything was first class, even the coffee shop downstairs. Not to mention the grocery store that is attached to the same building. The ultimate convenience right near the miracle Mile in Chicago, my most favorite place in the world.
Reviewed on 25 Nov 2025

Chicago luxury home suites
Downtown Chicago
Price was €3,945, price is now €2,762 per person
€2,762
per person
29 Dec - 4 Jan
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
10/10 Exceptional! (1 review)
Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job.
Reviewed on 26 Nov 2025

Pendry Chicago
Downtown Chicago
Price was €1,499, price is now €1,053 per person
€1,053
per person
29 Dec - 4 Jan
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
I thoroughly enjoyed my time at Pendry Chicago. I stayed in a tower king room. I originally was going to stay in a suite but the normal king room was very spacious for one person. The valet service was pretty quick and the valets were all very nice. The front desk clerk was extremely helpful and professional. I loved staying right on Michigan Ave and within walking distance to so many things. I read some reviews saying safety was a concern but I didn’t experience any safety issues. They lock the doors on Michigan Ave after a certain point to keep the flow of traffic thru a better monitored entrance. I also took an evening(beginning around 9:30pm) stroll around Millennium Park, down to Buckingham fountain and back up Michigan Ave to the river and the surroundings blocks around the hotel. At no point did I feel unsafe and would highly recommend this hotel to anyone coming to Chicago. The location is fantastic, the employees are amazing and the rooms are comfy. What more could you ask for?
Reviewed on 26 Nov 2025

Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was €1,330, price is now €1,018 per person
€1,018
per person
29 Dec - 4 Jan
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,002 reviews)
The Chicago Athletic Association Hotel is the most charming hotel in the city of Chicago. My wife and I recently got married in Chicago and one of the highlights of the weekend was hanging out at the hotel! It has a roaring 20's vibe with the dark woods in the main lobby and the large game room which is a fun place to get a drink and play chess/pool. Amazing location close to the Amtrak, Chicago subway, and the South shore railroad. And it's across the street from Millennium Park. Most importantly, the staff is very professional and attentive and will go above and beyond to make your stay perfect. I always stay at this hotel when I go to Chicago because of it's charm and service. I would never stay anywhere else because it's a truly unique hotel in an awesome location with the nicest and most professional staff. 10/10 recommend to anyone!
Reviewed on 20 Nov 2025
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

Clearing
Visitors to Clearing appreciate its restaurants. A visit to Wintrust Sports Complex and SeatGeek Stadium might round out your trip if you're looking to see more of the area.
Top hotels in Southwest Side

Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is €131 per night from 28 Dec to 29 Dec
€131
28 Dec - 29 Dec
includes taxes & fees
8.4/10 Very Good! (2,087 reviews)
Terrific, attentive staff, and clean room -- but a worn out room (peeling wallpaper, paint wearing off of door, scratched walls). This seemed at odds with the elegance of the rest of the place.
Reviewed on 23 Nov 2025

Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is €93 per night from 7 Dec to 8 Dec
€93
7 Dec - 8 Dec
includes taxes & fees
8.4/10 Very Good! (5,291 reviews)
All above.
Reviewed on 24 Nov 2025

Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is €84 per night from 7 Dec to 8 Dec
€84
7 Dec - 8 Dec
includes taxes & fees
8.8/10 Excellent! (3,388 reviews)
.
Reviewed on 26 Nov 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.
Popular places to visit

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.

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

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
96% of travellers recommend

Chicago: Navy Pier Centennial Wheel Ticket
€21
per adult
84% of travellers recommend

Wendella's 90-min Chicago River Architecture Tour
€39
per adult
94% of travellers recommend
Frequently asked questions
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Flights
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General
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