
Southern Wisconsin Romantic Holidays
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Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was HK$8,188, price is now HK$5,135 per person
HK$5,135
per person
4 Sept - 7 Sept
found 3 hours ago
Return flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
The good:
Staff was great
Location
Comfortable bed
The bad:
Extra daily charge that you are told about as you check in. I'm sure it's in the fine print but I saw nothing special that extra cost (6 nights it added up) got the guests and I think that's a real insult when we already paying a lot of $$.
Water pressure and heat of water terrible.
TV didn't work very well
Not much in room - small, no fridge, no microwave
I'd stay again in a pinch but will avoid - especially because of the inexplicable daily fee.
Reviewed on 11 Jul 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was HK$10,436, price is now HK$6,562 per person
HK$6,562
per person
4 Sept - 7 Sept
found 3 hours ago
Return flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (4,586 reviews)
Everyone raves about the breakfast and they are absolutely right. Great location, loved it.
Reviewed on 11 Jul 2026

Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was HK$11,047, price is now HK$7,137 per person
HK$7,137
per person
4 Sept - 7 Sept
found 3 hours ago
Return flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
We traveled with four kids. There was a noticeable lack of other children around. However the property was prepared to have them around. There was an entire play room with brand new puzzles and gently used toys to play with. The pool was usually fairly empty so my kids had fun there. The basketball court was generally empty as well. We got a lot of use out of all three spaces. The staff was friendly and helpful. And the coffee shop downstairs was a frequent stop as well.
Reviewed on 9 Jul 2026

Level Chicago - River North
Downtown Chicago
Save 100% on your flight
Price was HK$9,649, price is now HK$6,461 per person
HK$6,461
per person
4 Sept - 7 Sept
found 3 hours ago
Return flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Amazing and beautiful hotel with caring and helpful staff!
Reviewed on 8 Jul 2026

Omni Chicago Hotel
Downtown Chicago
Save 100% on your flight
Price was HK$8,076, price is now HK$5,426 per person
HK$5,426
per person
4 Sept - 7 Sept
found 3 hours ago
Return flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
Great location and a friendly staff made this a great experience. The rooms are very nice, but a little dated, which made it feel a little less clean. The staff was amazing, especially the doorman/bellman, Ham. He went out of his way help everytime we arrived or departed, he asked how our day was and offered directions. I really can’t speak highly enough of him. We didn’t utilize the restaurant while there, but I did visit the bar and they had an excellent selection of high end bourbons.
Reviewed on 11 Jul 2026
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View all tripsPrice found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was HK$11,678, price is now HK$8,214 per person
HK$8,214
per person
4 Sept - 7 Sept
found 3 hours ago
Return flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,910 reviews)
I love Trump hotels the absolute BEST
Reviewed on 10 Jul 2026

Nobu Hotel Chicago
Downtown Chicago
Save 100% on your flight
Price was HK$12,293, price is now HK$9,298 per person
HK$9,298
per person
4 Sept - 7 Sept
found 3 hours ago
Return flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (879 reviews)
Stunning hotel with really attentive staff, located in the heart of Chicago's West Loop neighborhood. You are surrounded by a ton of award-winning restaurants, shopping and also close to public transit. Rooms are spacious and are themed in a minimalistic Japanese onsen-style esthetic. We loved our stay here, though there are a few things to mention that made our stay less than a perfect 10. The bathroom is fully painted in black. Looks great, but terrible for styling your hair, if you have dark colored hair. Poor lighting concepts throughout the room and bathroom in general, which made it terrible for getting ready any time of the day. Closet area was dark, not great for getting dressed. Bedroom area was dark, not great for reading a book. Desk area is dark, not great for working remotely. Bathroom lighting is dark, not great if you are a woman trying to put on makeup. Housekeeping was fantastic and really knew how to personalize your stay, but they still knocked on the door when we had the "do not disturb" light on, which was very bothersome and woke us up a couple of times.
Reviewed on 6 Jul 2026
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See all available trips from Columbus to Southern Wisconsin
View all tripsPrice found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was HK$8,188, price is now HK$5,135 per person
HK$5,135
per person
4 Sept - 7 Sept
found 3 hours ago
Return flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
The good:
Staff was great
Location
Comfortable bed
The bad:
Extra daily charge that you are told about as you check in. I'm sure it's in the fine print but I saw nothing special that extra cost (6 nights it added up) got the guests and I think that's a real insult when we already paying a lot of $$.
Water pressure and heat of water terrible.
TV didn't work very well
Not much in room - small, no fridge, no microwave
I'd stay again in a pinch but will avoid - especially because of the inexplicable daily fee.
Reviewed on 11 Jul 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was HK$10,436, price is now HK$6,562 per person
HK$6,562
per person
4 Sept - 7 Sept
found 3 hours ago
Return flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (4,586 reviews)
Everyone raves about the breakfast and they are absolutely right. Great location, loved it.
Reviewed on 11 Jul 2026

Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was HK$11,047, price is now HK$7,137 per person
HK$7,137
per person
4 Sept - 7 Sept
found 3 hours ago
Return flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
We traveled with four kids. There was a noticeable lack of other children around. However the property was prepared to have them around. There was an entire play room with brand new puzzles and gently used toys to play with. The pool was usually fairly empty so my kids had fun there. The basketball court was generally empty as well. We got a lot of use out of all three spaces. The staff was friendly and helpful. And the coffee shop downstairs was a frequent stop as well.
Reviewed on 9 Jul 2026
Don't see what you're looking for?
See all available trips from Columbus to Southern Wisconsin
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
