Southern Wisconsin Adventure Holidays

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Top flight + Adventure hotel deals in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.
Eaglewood Resort and Spa

Eaglewood Resort and Spa

£847
per person
27 Oct - 2 Nov
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
8.8/10 Excellent! (1,304 reviews)
Level Chicago - River North

Level Chicago - River North

Downtown Chicago
£1,261
per person
27 Oct - 2 Nov
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,077 reviews)
Viceroy Chicago

Viceroy Chicago

Downtown Chicago
£1,344
per person
27 Oct - 2 Nov
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,282 reviews)
The Glen Club

The Glen Club

£943
per person
27 Oct - 2 Nov
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (391 reviews)
Great experience and will be back at some point!

Reviewed on 18 Sept 2026

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago
£1,007
per person
31 Oct - 5 Nov
found 18 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (3,269 reviews)
Great stay! Courteous staff

Reviewed on 21 Sept 2026

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5* Adventure holidays in Southern Wisconsin

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

The Peninsula Chicago

Downtown Chicago
£1,465
per person
14 Nov - 18 Nov
just found
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
Absolutely amazing. Warm welcomes, great atmosphere, beautiful city

Reviewed on 20 Sept 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£2,057
per person
24 Nov - 28 Nov
found 17 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Always great service and hospitality here. Rooms are spotless and attended to multiple times daily.

Reviewed on 20 Sept 2026

The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

Downtown Chicago
£1,895
per person
27 Oct - 2 Nov
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,001 reviews)
Staff was excellent.

Reviewed on 17 Sept 2026

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3 Night Adventure holidays in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£941
per person
12 Nov - 15 Nov
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Only the wall outlet near the beds didn't work ...just that...everything was great !! Excelent hotel

Reviewed on 21 Sept 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,095
per person
12 Nov - 15 Nov
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Always great service and hospitality here. Rooms are spotless and attended to multiple times daily.

Reviewed on 20 Sept 2026

Pendry Chicago

Pendry Chicago

Downtown Chicago
£993
per person
12 Nov - 15 Nov
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,146 reviews)
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4 Night Adventure holidays in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
£1,161
per person
22 Oct - 26 Oct
found 7 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (561 reviews)
Amazing place to stay in Chicago!

Reviewed on 18 Sept 2026

The Emily Hotel

The Emily Hotel

Downtown Chicago
£1,315
per person
22 Oct - 26 Oct
found 7 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,338 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,564
per person
22 Oct - 26 Oct
found 7 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Always great service and hospitality here. Rooms are spotless and attended to multiple times daily.

Reviewed on 20 Sept 2026

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.