
Far Southwest Side Romantic Vacations
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Top Romantic vacation packages in Far Southwest Side
Price found within the past 48 hours. Click for updated prices.

Level Chicago – Old Town
Downtown Chicago
Price was ¥218,668, price is now ¥165,134 per person
¥165,134
per person
Feb 19 - Feb 23
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Room was spotless, all the kitchen amenities were provided such as a Nespresso machine with refills, electric kettle, dishes, utensils, pots, and pans. The refrigerator has a water dispenser inside full-size freezer microwave dishwasher. They provide dishwashing detergent and dish soap. Paper towels. Stackable washer and dryer they supply a single sample of laundry detergent to do laundry then you’re on your own. Aldi is on the first floor so if you need anything grocery is available. there is a café attached to the building. Workout area is immaculately cleaned every day. There is a game room a large area to watch TV. we did not bring our pet, but there is an area on the rooftop for pets to run around and there’s green space down below. A full basketball court and an area for children to play. it was winter so the pool and hot tub were closed. they provide fresh linens and towels as needed. They are very prompt and answer the phone quickly. The parking is secure and well lit. Location is in a safe neighborhood. Across the street is disco pancakes for breakfast. Target is just down the road and CVS and Jewel grocery stores. This is our second time staying. When we do stay, we stay about a week. It is quiet. Great views.
Reviewed on Dec 3, 2025

The Emily Hotel
Downtown Chicago
Price was ¥264,560, price is now ¥189,924 per person
¥189,924
per person
Feb 19 - Feb 23
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay.
Reviewed on Nov 26, 2025

Hilton Chicago O'Hare Airport
O'Hare
Price was ¥297,437, price is now ¥229,520 per person
¥229,520
per person
Feb 14 - Feb 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
Staff at desk. I was exhausted after hours of promises then delays then a total cancel at the airport. He was awesome.
Reviewed on Dec 3, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥370,092, price is now ¥293,567 per person
¥293,567
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
It's always perfection at the Trump. King suite with Lake view is the ultimate
Reviewed on Dec 2, 2025

The Peninsula Chicago
Downtown Chicago
Price was ¥353,515, price is now ¥288,612 per person
¥288,612
per person
Feb 22 - Feb 27
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Excellent service throughout the hotel
Reviewed on Nov 29, 2025
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View all trips5* Romantic vacations in Far Southwest Side
Price found within the past 48 hours. Click for updated prices.

Nobu Hotel Chicago
Downtown Chicago
Price was ¥277,688, price is now ¥245,355 per person
¥245,355
per person
Feb 4 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (748 reviews)
The sink clogged at some point the staff was not that attentive
Reviewed on Nov 29, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥370,092, price is now ¥293,567 per person
¥293,567
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
It's always perfection at the Trump. King suite with Lake view is the ultimate
Reviewed on Dec 2, 2025

The Peninsula Chicago
Downtown Chicago
Price was ¥353,515, price is now ¥288,612 per person
¥288,612
per person
Feb 22 - Feb 27
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Excellent service throughout the hotel
Reviewed on Nov 29, 2025
Don't see what you're looking for?
See all available trips from Tokyo to Far Southwest Side
View all trips3 Night Romantic vacations in Far Southwest Side
Price found within the past 48 hours. Click for updated prices.

DoubleTree by Hilton Chicago Schaumburg
Price was ¥200,232, price is now ¥185,827 per person
¥185,827
per person
Jan 24 - Jan 27
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
7.2/10 Good! (1,003 reviews)
The room could use some help on cleanliness but it wasn’t bad and the staff was amazing always helpful and cheerful.
Reviewed on Nov 28, 2025

Hilton Chicago O'Hare Airport
O'Hare
Price was ¥239,958, price is now ¥212,132 per person
¥212,132
per person
Jan 24 - Jan 27
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
Staff at desk. I was exhausted after hours of promises then delays then a total cancel at the airport. He was awesome.
Reviewed on Dec 3, 2025

Don't see what you're looking for?
See all available trips from Tokyo to Far Southwest Side
View all trips4 Night Romantic vacations in Far Southwest Side
Price found within the past 48 hours. Click for updated prices.

Level Chicago – Old Town
Downtown Chicago
Price was ¥218,668, price is now ¥165,134 per person
¥165,134
per person
Feb 19 - Feb 23
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Room was spotless, all the kitchen amenities were provided such as a Nespresso machine with refills, electric kettle, dishes, utensils, pots, and pans. The refrigerator has a water dispenser inside full-size freezer microwave dishwasher. They provide dishwashing detergent and dish soap. Paper towels. Stackable washer and dryer they supply a single sample of laundry detergent to do laundry then you’re on your own. Aldi is on the first floor so if you need anything grocery is available. there is a café attached to the building. Workout area is immaculately cleaned every day. There is a game room a large area to watch TV. we did not bring our pet, but there is an area on the rooftop for pets to run around and there’s green space down below. A full basketball court and an area for children to play. it was winter so the pool and hot tub were closed. they provide fresh linens and towels as needed. They are very prompt and answer the phone quickly. The parking is secure and well lit. Location is in a safe neighborhood. Across the street is disco pancakes for breakfast. Target is just down the road and CVS and Jewel grocery stores. This is our second time staying. When we do stay, we stay about a week. It is quiet. Great views.
Reviewed on Dec 3, 2025

The Emily Hotel
Downtown Chicago
Price was ¥264,560, price is now ¥189,924 per person
¥189,924
per person
Feb 19 - Feb 23
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay.
Reviewed on Nov 26, 2025

The Hoxton Chicago
Downtown Chicago
Price was ¥216,436, price is now ¥181,397 per person
¥181,397
per person
Feb 19 - Feb 23
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Nice room - a little small. Staff were friendly and helpful. The lounge’s and bars were great.
Reviewed on Nov 26, 2025
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See all available trips from Tokyo to Far Southwest Side
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
