Far Southeast Side Cheap Vacations
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Flight and Cheap hotel deals in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Downtown Chicago
CA $1,030
per person
Dec 2 - Dec 9
found 22 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.6/10 Excellent! (1,011 reviews)
Elevators not all working and could not get heat in the room over a rainy and cool weekend
Reviewed on Sep 20, 2026
Level Chicago – Old Town
Downtown Chicago
CA $1,508
per person
Dec 2 - Dec 9
found 22 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (520 reviews)
Amazing stay. Love the balcony view. Parking was easy and accessible. Will be back!
Reviewed on Sep 19, 2026
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View all trips5* Cheap holidays in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $2,896
per person
Dec 2 - Dec 9
found 22 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Always great service and hospitality here. Rooms are spotless and attended to multiple times daily.
Reviewed on Sep 20, 2026
The Peninsula Chicago
Downtown Chicago
CA $3,573
per person
Dec 2 - Dec 9
found 22 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
Absolutely amazing. Warm welcomes, great atmosphere, beautiful city
Reviewed on Sep 20, 2026
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View all trips3 Night Cheap holidays in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,446
per person
Nov 5 - Nov 8
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Always great service and hospitality here. Rooms are spotless and attended to multiple times daily.
Reviewed on Sep 20, 2026
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View all trips4 Night Cheap holidays in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
CA $1,077
per person
Oct 21 - Oct 25
found 9 hours ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
8.2/10 Very good! (3,012 reviews)
Friendly staff. Cleanliness was subpar in common areas.
Reviewed on Sep 20, 2026
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View all tripsThings to do
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% 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.
