Far Southwest Side Holidays
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Top Flight + Hotel Deals in Far Southwest Side
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was €864, price is now €622 per person
€622
per person
31 Oct - 3 Nov
found 17 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (2,096 reviews)
The staff from the start were very nice and helpful. The hotel was clean loved the location of the hotel. Will definitely try booking ag this hotel next year
Reviewed on 2 Sep 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €3,218, price is now €2,145 per person
€2,145
per person
5 Nov - 12 Nov
found 3 hours ago
Return direct flight included
Palma de Mallorca (PMI) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
Best, very clean, best view, really enjoyed the stay!
Reviewed on 2 Sep 2025
Level Chicago – Old Town
Downtown Chicago
Price was €945, price is now €643 per person
€643
per person
31 Oct - 3 Nov
found 17 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
Everything was perfect. Be aware of the expensive it is to park in Chicago.
Reviewed on 2 Sep 2025
The Emily Hotel
Downtown Chicago
Price was €2,604, price is now €1,781 per person
€1,781
per person
5 Nov - 12 Nov
found 3 hours ago
Return direct flight included
Palma de Mallorca (PMI) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
Great hotel, especially for the price, nice area, would go back again if I’m in Chicago.
Reviewed on 2 Sep 2025
The Peninsula Chicago
Downtown Chicago
Save 100% on your flight
Price was €1,964, price is now €1,431 per person
€1,431
per person
31 Oct - 3 Nov
found 17 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Always an amazing place! We keep comi
Reviewed on 2 Sep 2025
Where 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 a few reasons travellers visit Ashburn. Though there aren't many top sights in the neighbourhood, you can visit Chicago Ridge Shopping Mall and Balzekas Museum of Lithuanian Culture, a few notable attractions nearby.
Top hotels in Far Southwest Side
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €198 per night from 15 Sept to 16 Sept
€198
15 Sept - 16 Sept
includes taxes & fees
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
The price is €169 per night from 4 Sept to 5 Sept
€169
4 Sept - 5 Sept
includes taxes & fees
The Wade
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €168 per night from 22 Sept to 23 Sept
€168
22 Sept - 23 Sept
includes taxes & fees
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
4.5/5(40 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
4.5/5(14 reviews)
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
4/5(125 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Far Southwest Side
Wendella's 90-min Chicago River Architecture Tour
€35
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
€39
per adult
96% of travellers recommend
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