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Top Adventure vacation packages in Chicago

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

Hotel Chicago Downtown, Autograph Collection by Marriott

Downtown Chicago

￥147,206

per person

Feb 19 - Feb 23

just found

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9/10 Wonderful! (1,003 reviews)

Staff were very pleasant and helpful. We will definitely be back.

Reviewed on Nov 26, 2025

Swissotel - Chicago

Downtown Chicago

￥275,402

per person

Jan 17 - Jan 21

just found

Roundtrip flight included

Kitakyushu (KKJ) to Chicago (ORD)

9/10 Wonderful! (2,947 reviews)

Amazing view, service was outstanding!! Simona was above and beyond! Best place to stay in Chicago and I have stayed at many! Secret little nook back there!

Reviewed on Dec 2, 2025

The Peninsula Chicago

Downtown Chicago

￥247,778

per person

Feb 19 - Feb 23

just found

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

Pendry Chicago

Downtown Chicago

￥167,091

per person

Feb 4 - Feb 8

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.4/10 Exceptional! (1,130 reviews)

Inviting lobby area with comfortable bar on the side. Excellent cocktails! 19th floor room with roomy bathroom & excellent water pressure. Soft, comfortable sheets on moderately firm mattresses. Very prompt room service with nice choices 24/7 (we ordered at midnight). Located about 2 blocks from Miracle Mile. On top of that, customer service was outstanding!

Reviewed on Dec 1, 2025

The Westin Chicago River North

Downtown Chicago

￥266,014

per person

Feb 19 - Feb 23

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9/10 Wonderful! (1,002 reviews)

There was dirty socks in the bathroom and left over food in the mini fridge. The body wash dispenser in the shower was empty. Poor maid service. The place is in a great location but interiors are outdated.

Reviewed on Dec 1, 2025

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5* Adventure vacations in Chicago

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

The Peninsula Chicago

Downtown Chicago

￥247,778

per person

Feb 19 - Feb 23

just found

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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See all available trips from Tokyo to Chicago

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4 Night Adventure vacations in Chicago

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

Hotel Chicago Downtown, Autograph Collection by Marriott

Downtown Chicago

￥147,206

per person

Feb 19 - Feb 23

just found

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9/10 Wonderful! (1,003 reviews)

Staff were very pleasant and helpful. We will definitely be back.

Reviewed on Nov 26, 2025

Swissotel - Chicago

Downtown Chicago

￥275,402

per person

Jan 17 - Jan 21

just found

Roundtrip flight included

Kitakyushu (KKJ) to Chicago (ORD)

9/10 Wonderful! (2,947 reviews)

Amazing view, service was outstanding!! Simona was above and beyond! Best place to stay in Chicago and I have stayed at many! Secret little nook back there!

Reviewed on Dec 2, 2025

Hyatt Place Chicago/River North

Downtown Chicago

￥275,285

per person

Jan 17 - Jan 21

just found

Roundtrip flight included

Kitakyushu (KKJ) to Chicago (ORD)

9.2/10 Wonderful! (1,508 reviews)

Huge room, spacious, and free breakfast!

Reviewed on Dec 2, 2025

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See all available trips from Tokyo to Chicago

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Top Adventure Chicago Hotels

Palmer House a Hilton Hotel

17 E Monroe St Chicago IL

12 min drive from Wrigley Field

Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...

8.4/10 Very Good! (2,121 reviews)

W

Reviewed on Dec 2, 2025

Hyatt Regency McCormick Place Chicago

2233 S Martin Luther King Dr Chicago IL

16 min drive from Wrigley Field

Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...

9/10 Wonderful! (1,035 reviews)

Would visit again

Reviewed on Nov 21, 2025

Hyatt Regency Chicago

151 East Wacker Dr Chicago IL

11 min drive from Wrigley Field

Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...

9.2/10 Wonderful! (3,414 reviews)

I had a first time to visit Chicago with my family. We walked around the city, good experiences😊

Reviewed on Nov 29, 2025

See all 5,594 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.