Far Southeast Side Mountain Vacations
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Flight and Mountain hotel deals in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.
L7 Chicago by LOTTE
Downtown Chicago
Price was CA $1,338, price is now CA $957 per person
CA $957
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (4,232 reviews)
This hotel and their staff exceeded our expectations. From the first greeting at the door from a smiling Antonio to the check-in experience with Alex and Meggy, we could not have been happier! We were treated like royalty, the amenities offered were wonderful, and the location can’t be beat. We will definitely stay again and again!
Reviewed on Jun 27, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $3,635, price is now CA $2,437 per person
CA $2,437
per person
Sep 12 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (495 reviews)
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well
Reviewed on Jun 26, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $1,606, price is now CA $1,100 per person
CA $1,100
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,034 reviews)
Really plan ahead when it comes to parking. You’ll get ticketed for just trying to put your things in your vehicle.
Reviewed on Jun 19, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,773, price is now CA $1,251 per person
CA $1,251
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
The room was very clean and the view to the lake from the window was stunning
Reviewed on Jun 28, 2026
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See all available trips from Columbus to Far Southeast Side
View all trips5* Mountain holidays in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,997, price is now CA $1,513 per person
CA $1,513
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,899 reviews)
Great location, wonderful staff.
Reviewed on Jun 26, 2026
The Langham, Chicago
Downtown Chicago
Price was CA $2,469, price is now CA $1,893 per person
CA $1,893
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
Love this hotel! Staff is extremely welcoming, knowledgeable about the area, rooms are nice and cozy, it's quiet, and you can't beat the location!! We will be back - without doubt!
Reviewed on Jun 26, 2026
Nobu Hotel Chicago
Downtown Chicago
Price was CA $2,042, price is now CA $1,654 per person
CA $1,654
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (869 reviews)
Shower bombs would be a good incentive. Really enjoyed the scenery as well as the customer service.
Reviewed on Jun 27, 2026
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See all available trips from Columbus to Far Southeast Side
View all trips3 Night Mountain holidays in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North
Downtown Chicago
Price was CA $1,606, price is now CA $1,100 per person
CA $1,100
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,034 reviews)
Really plan ahead when it comes to parking. You’ll get ticketed for just trying to put your things in your vehicle.
Reviewed on Jun 19, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,773, price is now CA $1,251 per person
CA $1,251
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
The room was very clean and the view to the lake from the window was stunning
Reviewed on Jun 28, 2026
Don't see what you're looking for?
See all available trips from Columbus to Far Southeast Side
View all trips4 Night Mountain holidays in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection
Downtown Chicago
Price was CA $1,297, price is now CA $919 per person
CA $919
per person
Aug 30 - Sep 3
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (126 reviews)
Always a pleasure and a great location
Reviewed on Jun 24, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,401, price is now CA $983 per person
CA $983
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (504 reviews)
Upscale amazing stay in trendy neighborhood in Chcago. Walking distance to coffee shops, great restaurants. The amenities were beyond what I expected/ great lap pool, hot tubs, sauna steam room and amazing gym with enough equipment to do a full strength training workout. We will stay here again!
Reviewed on Jun 25, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,431, price is now CA $1,747 per person
CA $1,747
per person
Aug 7 - Aug 11
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (495 reviews)
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well
Reviewed on Jun 26, 2026
Don't see what you're looking for?
See all available trips from Columbus to Far Southeast Side
View all tripsThings to do
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
88% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $62
per adult
94% of travellers recommend
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