Northwest Indiana Mountain Vacations
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Flight and Mountain hotel deals in Northwest Indiana
Price found within the past 48 hours. Click for updated prices.
Omni Chicago Hotel
Downtown Chicago
Price was CA $1,259, price is now CA $918 per person
CA $918
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,813 reviews)
Located in a walkable area near many Chicago attractions. We had a delicious breakfast in the hotel restaurant and the bar is nice. Room was large and comfortable
Reviewed on Jun 23, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,544, price is now CA $1,096 per person
CA $1,096
per person
Aug 3 - Aug 8
found 15 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (2,767 reviews)
Great location, we were able to walk everywhere we wanted to see. The red line is about a 10 minute walk if you are heading to Wrigley.
Reviewed on Jun 26, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,991, price is now CA $2,125 per person
CA $2,125
per person
Aug 3 - Aug 8
just found
Roundtrip flight included
Hamilton (YHM) 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
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View all trips5* Mountain holidays in Northwest Indiana
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,052, price is now CA $1,605 per person
CA $1,605
per person
Sep 16 - Sep 18
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
It was everything I expected! The staff was amazing. Everything ran smoothly. I would say the pool could use a little updating. Everything was delightful. Definitely will be back.
Reviewed on Jun 24, 2026
Nobu Hotel Chicago
Downtown Chicago
Price was CA $2,292, price is now CA $1,865 per person
CA $1,865
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (869 reviews)
My stay was remarkable! Staff was extremely friendly, room clean, in room dining food was delicious!
Reviewed on Jun 21, 2026
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View all trips3 Night Mountain holidays in Northwest Indiana
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $960, price is now CA $667 per person
CA $667
per person
Sep 2 - Sep 5
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,767 reviews)
Great location, we were able to walk everywhere we wanted to see. The red line is about a 10 minute walk if you are heading to Wrigley.
Reviewed on Jun 26, 2026
The Talbott, Autograph Collection
Downtown Chicago
Price was CA $1,136, price is now CA $793 per person
CA $793
per person
Sep 2 - Sep 5
found 24 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 - River North
Downtown Chicago
Price was CA $1,627, price is now CA $1,226 per person
CA $1,226
per person
Sep 4 - Sep 7
found 24 hours 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
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See all available trips from Columbus to Northwest Indiana
View all trips4 Night Mountain holidays in Northwest Indiana
Price found within the past 48 hours. Click for updated prices.
Omni Chicago Hotel
Downtown Chicago
Price was CA $1,259, price is now CA $918 per person
CA $918
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,813 reviews)
Located in a walkable area near many Chicago attractions. We had a delicious breakfast in the hotel restaurant and the bar is nice. Room was large and comfortable
Reviewed on Jun 23, 2026
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View all tripsThings to do
An Epic Scavenger Hunt: Fun With Fort Wayne
CA $17
per adult
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