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Top Cheap vacation packages in Chicago

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

Hotel Saint Clair- Magnificent Mile

Downtown Chicago

￥144,414

per person

Feb 19 - Feb 23

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

8.2/10 Very Good! (1,769 reviews)

Clean room. Nice location.

Reviewed on Dec 3, 2025

Hotel Felix River North/Magnificent Mile

Downtown Chicago

￥264,068

per person

Jan 17 - Jan 21

found 19 hours ago

Roundtrip flight included

Kitakyushu (KKJ) to Chicago (ORD)

8.2/10 Very Good! (2,365 reviews)

Great welcome. Room looks good.

Reviewed on Dec 3, 2025

River Hotel

Downtown Chicago

￥148,512

per person

Feb 19 - Feb 23

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

8.8/10 Excellent! (4,800 reviews)

Ron helped us with luggage storage and then check in. Excellent customer service!! So far our stay has been great!!

Reviewed on Dec 4, 2025

Club Quarters Hotel, Central Loop, Chicago

Downtown Chicago

￥150,154

per person

Feb 4 - Feb 8

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

8.8/10 Excellent! (3,289 reviews)

Clean and comfy room with great location

Reviewed on Dec 3, 2025

Central Loop Hotel

Downtown Chicago

￥150,154

per person

Feb 4 - Feb 8

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

8.6/10 Excellent! (1,896 reviews)

This was our second time staying here. It's clean, cheap, and in a convenient location.

Reviewed on Dec 2, 2025

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4 Night Cheap vacations in Chicago

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

Country Inn & Suites by Radisson, Chicago O'Hare South, IL

￥139,206

per person

Feb 19 - Feb 23

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

7.2/10 Good! (1,168 reviews)

The staff was great, the hotel was outdated, and the free breakfast tasted microwaved. But hey for the price I got the room for I can’t be too mad. Only real disappointment was the pool area that looks unkept. Not to mention it reeks of wet dog when you enter and no towels were available. I tired out the jacuzzi for 15mins I couldn’t stand the smell anymore

Reviewed on Dec 3, 2025

Hotel Felix River North/Magnificent Mile

Downtown Chicago

￥264,068

per person

Jan 17 - Jan 21

found 19 hours ago

Roundtrip flight included

Kitakyushu (KKJ) to Chicago (ORD)

8.2/10 Very Good! (2,365 reviews)

Great welcome. Room looks good.

Reviewed on Dec 3, 2025

Hotel Saint Clair- Magnificent Mile

Downtown Chicago

￥144,414

per person

Feb 19 - Feb 23

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

8.2/10 Very Good! (1,769 reviews)

Clean room. Nice location.

Reviewed on Dec 3, 2025

Don't see what you're looking for?

See all available trips from Tokyo to Chicago

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Top Cheap Chicago Hotels

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. ...

7.8/10 Good! (2,621 reviews)

Habitación pequeña pero muy confortable, baño completo y bien equipado, excelente ubicación del hotel.

Reviewed on Nov 29, 2025

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 ...

7.2/10 Good! (2,485 reviews)

Yes

Reviewed on Nov 29, 2025

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! (1,716 reviews)

Room is pretty clean. Most of the staff is friendly except one front desk woman.

Reviewed on Nov 30, 2025

See all 5,599 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.