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Top Cheap vacation packages in Chicago

Price found within the past 48 hours. Click for updated prices.

Freehand Chicago

Downtown Chicago

￥245,420

per person

Jun 12 - Jun 15

found 19 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

8/10 Very Good! (2,893 reviews)

The property was located literally in the center of downtown. Everything was accessible and walkable. All the major attractions were within 2 to 5 km of what Chicago is really advertise to be. Staff was great open bar was amazing. Vibes were nice and other guests were on the same vibe levels.

Reviewed on Apr 28, 2026

Hotel Felix River North/Magnificent Mile

Downtown Chicago

￥332,043

per person

Jun 7 - Jun 10

found 21 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

8.2/10 Very Good! (2,636 reviews)

Kind staff and helpful, nice rooms, wish there was a fridge in the room.

Reviewed on Apr 27, 2026

River Hotel

Downtown Chicago

￥330,680

per person

Jun 7 - Jun 10

found 21 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

8.8/10 Excellent! (5,116 reviews)

Great place,staff and location we will be back again for the 3rd time

Reviewed on Apr 27, 2026

Club Quarters Hotel, Central Loop, Chicago

Downtown Chicago

￥323,500

per person

Jun 7 - Jun 10

found 21 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

8.8/10 Excellent! (3,447 reviews)

great views and clean rooms!

Reviewed on Apr 28, 2026

Central Loop Hotel

Downtown Chicago

￥323,500

per person

Jun 7 - Jun 10

found 21 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

8.6/10 Excellent! (2,093 reviews)

The room was dingy and outdated.

Reviewed on Apr 27, 2026

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See all available trips from Tokyo to Chicago

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3 Night Cheap vacations in Chicago

Price found within the past 48 hours. Click for updated prices.

Club Quarters Hotel, Central Loop, Chicago

Downtown Chicago

￥323,500

per person

Jun 7 - Jun 10

found 21 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

8.8/10 Excellent! (3,447 reviews)

great views and clean rooms!

Reviewed on Apr 28, 2026

Hotel Felix River North/Magnificent Mile

Downtown Chicago

￥332,043

per person

Jun 7 - Jun 10

found 21 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

8.2/10 Very Good! (2,636 reviews)

Kind staff and helpful, nice rooms, wish there was a fridge in the room.

Reviewed on Apr 27, 2026

River Hotel

Downtown Chicago

￥330,680

per person

Jun 7 - Jun 10

found 21 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

8.8/10 Excellent! (5,116 reviews)

Great place,staff and location we will be back again for the 3rd time

Reviewed on Apr 27, 2026

Don't see what you're looking for?

See all available trips from Tokyo to Chicago

View all trips

Top Cheap Chicago Hotels

Motel 6 Elk Grove Village, IL - O'Hare

2881 Touhy Ave Elk Grove Village IL

22 min drive from Wrigley Field

Stay at this motel in Elk Grove Village. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...

7.8/10 Good! (1,928 reviews)

They have 14 days stay policy 😃😄 it is absurd

Reviewed on Apr 28, 2026

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

13 min drive from Wrigley Field

Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...

7.4/10 Good! (2,566 reviews)

Located close to several restaurants and public transport. Staff was wonderful. But the hotel itself was quite run down and dilapidated. Old carpet, bed was sinking down in the middle, scuffs, dings and scratches on virtually ever surface, poor workmanship everywhere, exposed piping and wiring in ...

Reviewed on Apr 28, 2026

Freehand Chicago

19 East Ohio Street Chicago IL

10 min drive from Wrigley Field

Stay at this hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...

8/10 Very Good! (2,923 reviews)

I was very happy with the location. I would tell people it is a good place for stay over and if you have good weather to be outside Wouldn’t want to spend a lot of time in there pretty much used it to sleep and then get going in the morning. The price was unbelievable I would like to find a few like ...

Reviewed on Apr 28, 2026

See all 5,562 properties in Chicago

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.