Southern Wisconsin Luxury Holidays

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Top flight + Luxury hotel deals in Southern Wisconsin

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

Hotel Riu Plaza Chicago

Downtown Chicago
£1,039
per person
29 Sept - 3 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
I stayed here for about five days with my boyfriend. The hotel was very nice and the staff was very helpful. The rooftop is beautiful with a great view. It’s right in the middle of downtown so it’s very walkable to any places if you’re planning on spending a lot of time in the city. I would recommend finding parking offsite compared to the hotel because that’s what’s easiest if you are traveling via car a lot and also the food isn’t very great but it’s just fine. Overall, this was a very nice day and I would most definitely recommend it if you’re staying with a partner or family.

Reviewed on 17 Aug 2026

Kinzie Hotel

Kinzie Hotel

Downtown Chicago
£1,103
per person
25 Oct - 30 Oct
found 16 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (2,161 reviews)
Muy buen lugar pero personal debe ser más servicial y buscar la manera de que alguien ayude con el idioma español. Y no solo ignorar a los huéspedes.

Reviewed on 17 Aug 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
£1,250
per person
22 Oct - 26 Oct
found 16 hours ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
£1,153
per person
1 Oct - 5 Oct
found 17 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
My go to place to stay. Luxurious, travel-friendly rooms, excellent pool/hot tub area outside, and great workout facilities. Fantastic location next to Fulton Market. The desk staff is always exceptional and helpful.

Reviewed on 12 Aug 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,924
per person
26 Sept - 2 Oct
found 23 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
This is an excellent 5 star hotel. So accommodating in every way possible. This is the second time I have stayed at this Chicago property.

Reviewed on 16 Aug 2026

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5* Luxury holidays in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,924
per person
26 Sept - 2 Oct
found 23 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
This is an excellent 5 star hotel. So accommodating in every way possible. This is the second time I have stayed at this Chicago property.

Reviewed on 16 Aug 2026

Park Hyatt Chicago

Park Hyatt Chicago

Downtown Chicago
£2,324
per person
26 Sept - 2 Oct
found 23 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
£2,695
per person
26 Sept - 2 Oct
found 23 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Don't see what you're looking for?
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4 Night Luxury 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
£1,039
per person
29 Sept - 3 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
I stayed here for about five days with my boyfriend. The hotel was very nice and the staff was very helpful. The rooftop is beautiful with a great view. It’s right in the middle of downtown so it’s very walkable to any places if you’re planning on spending a lot of time in the city. I would recommend finding parking offsite compared to the hotel because that’s what’s easiest if you are traveling via car a lot and also the food isn’t very great but it’s just fine. Overall, this was a very nice day and I would most definitely recommend it if you’re staying with a partner or family.

Reviewed on 17 Aug 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
£1,250
per person
22 Oct - 26 Oct
found 16 hours ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
£1,153
per person
1 Oct - 5 Oct
found 17 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
My go to place to stay. Luxurious, travel-friendly rooms, excellent pool/hot tub area outside, and great workout facilities. Fantastic location next to Fulton Market. The desk staff is always exceptional and helpful.

Reviewed on 12 Aug 2026

Don't see what you're looking for?
See all available trips from Dublin to Southern Wisconsin
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All you need to know about luxury holidays in Southern Wisconsin

What can I expect from a luxury Southern Wisconsin holiday?

Luxury on holiday is all about relaxing and feeling good. Whether you choose a sumptuous spa, Michelin-starred restaurant or super-king bed is your call. Use our amenities filters to find the things that tick all your boxes.

How can I find all-inclusive luxury holidays in Southern Wisconsin?

Tick the all-inclusive and 5-star filters to find the crème de la crème of Southern Wisconsin holidays. With everything included in the package price, you can drink and dine to your heart’s content, without worrying about that bill at the end.

Can I book a cheap luxury holiday to Southern Wisconsin?

A luxury holiday doesn’t have to break the bank. Travel out of peak season, choose a hotel or resort a little way out or go for a last-minute getaway and you’ll find some cracking deals. Sort by price to find luxury holidays to Southern Wisconsin starting at £1,039. Prices and availability are subject to change. Additional terms may apply.

Are there luxury spa holidays in Southern Wisconsin?

For sunset massages on the shoreline and view-filled saunas, use our spa filter to find your ideal Southern Wisconsin spa hotel. Book a whole weekend soaking away your stresses, or hop into the spa after the beach, some golf or a local advent-ahhhh.

What should I look for when booking a luxury family holiday in Southern Wisconsin?

Luxury isn’t just for adults. Those little touches designed for little people make a family holiday genuinely stress free … which is the greatest luxury of all. Look for spacious suites, pools toddlers can splash in, and breakfast buffets with waffles, pancakes and Nutella galore.

Can I book luxury last-minute holidays to Southern Wisconsin?

You can wangle a top-notch luxury holiday in Southern Wisconsin for a fraction of the normal price by booking last minute. Just enter your dates and see what’s available – if you’re flexible ... even better!

Can I book a luxury holiday in Southern Wisconsin with free cancellation and/or flexible dates?

If you’re splashing out on a luxury holiday, make sure your money is safe by booking with free cancellation. Just use the fully refundable filter and make sure you read all the terms and conditions.

Why should I book my luxury travel to Southern Wisconsin with Expedia?

Nobody does luxury quite like Expedia. With so many gorgeous properties in Southern Wisconsin to choose from, as well as access to first-class flight deals and hire cars with horsepower, there’s no better place to book.

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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.