Southwest Side Holidays from £694
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Packages with flights are ATOL protected
Top Southwest Side Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was £976, price is now £694 per person
£694
per person
18 Nov - 22 Nov
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9/10 Wonderful! (1,992 reviews)
Nice hotel but room was extremely small.
Reviewed on 11 Sept 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,937, price is now £1,240 per person
£1,240
per person
23 Oct - 28 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
You were being taken care of felt like home away from home good job to the staff at the Trump tower Chicago
Reviewed on 12 Sept 2025
The Emily Hotel
Downtown Chicago
Price was £1,591, price is now £1,071 per person
£1,071
per person
23 Oct - 28 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,195 reviews)
The rooms were not very well decorated. The furniture used in the room looks like furniture from a detention house. Not my favorite.
Reviewed on 8 Sept 2025
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was £1,321, price is now £945 per person
£945
per person
23 Oct - 28 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9/10 Wonderful! (1,014 reviews)
First time but won’t be the last. Very nice place with lots to do right around there.
Reviewed on 9 Sept 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
Garfield Ridge
Be sure to check out the restaurants and churches while you're strolling through Garfield Ridge, and hop on the metro at Midway Station to see more of the surrounding area.
Southwest Side Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
Top hotels in Southwest Side
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £105 per night from 13 Sept to 14 Sept
£105
13 Sept - 14 Sept
includes taxes & fees
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £150 per night from 22 Sept to 23 Sept
£150
22 Sept - 23 Sept
includes taxes & fees
Freehand Chicago
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £100 per night from 21 Sept to 22 Sept
£100
21 Sept - 22 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
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
Wendella's 90-min Chicago River Architecture Tour
£33
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
£33
per adult
96% of travellers recommend
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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. Flight-inclusive packages are ATOL protected.
