Southern Wisconsin Romantic Holidays

Book a Romantic Hotel + Flight or Car together to unlock savings

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    Packages with flights are ATOL protected

Top flight + Romantic hotel deals in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
£923
per person
22 Nov - 29 Nov
found 5 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
Save 100% on your flight
£1,389
per person
7 Nov - 14 Nov
found 5 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,010 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
£1,418
per person
22 Oct - 28 Oct
found 1 day ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
We have stayed with RIU in major cities across the US as well as internationally. We are happy with all things across the board, but especially the staff and people. And the facilities are fantastic as each has its own personality, depending on where you stay. They have everything to make our stays comfortable and fun and that’s why we continue our stay time and time again.

Reviewed on 22 Sept 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
£1,262
per person
22 Oct - 28 Oct
found 1 day ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
Great stay!

Reviewed on 22 Sept 2026

The Emily Hotel

The Emily Hotel

Downtown Chicago
£983
per person
22 Nov - 29 Nov
found 5 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,338 reviews)
It was ok

Reviewed on 21 Sept 2026

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5* Romantic holidays in Southern Wisconsin

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

Nobu Hotel Chicago

Downtown Chicago
£1,592
per person
28 Nov - 2 Dec
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (922 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
£1,857
per person
22 Oct - 28 Oct
found 1 day ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
£2,418
per person
22 Oct - 28 Oct
found 1 day ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
Don't see what you're looking for?
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3 Night Romantic holidays in Southern Wisconsin

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

Swissotel - Chicago

Downtown Chicago
£890
per person
22 Oct - 25 Oct
found 6 hours ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
Great stay!

Reviewed on 22 Sept 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

Downtown Chicago
£902
per person
22 Oct - 25 Oct
found 6 hours ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9/10 Wonderful! (3,881 reviews)
Great location and classy.

Reviewed on 22 Sept 2026

Stay One Chicago

Stay One Chicago

Downtown Chicago
£1,078
per person
22 Oct - 25 Oct
found 6 hours ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
7.8/10 Good! (12 reviews)
Very nice and clean property. Beds were extremely comfortable and the room was spacious! Loved it!

Reviewed on 20 Sept 2026

Don't see what you're looking for?
See all available trips from Birmingham to Southern Wisconsin
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4 Night Romantic 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 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (561 reviews)
I loved the balcony and the great view! The kitchenette was a plus along with the provided utensils and necessary items. The laundry are was not something that I used but I could see how it would be a bonus feature. The area by the bed was a little cramped, but it ended up being comfortable. The staff was extremely friendly and helpful and the check in was seamless. The elevators were especially private and convenient. Overall, the extra $ that I paid for my stay was well worth it!

Reviewed on 21 Sept 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,306
per person
22 Oct - 26 Oct
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
We have stayed with RIU in major cities across the US as well as internationally. We are happy with all things across the board, but especially the staff and people. And the facilities are fantastic as each has its own personality, depending on where you stay. They have everything to make our stays comfortable and fun and that’s why we continue our stay time and time again.

Reviewed on 22 Sept 2026

The Emily Hotel

The Emily Hotel

Downtown Chicago
£1,315
per person
22 Oct - 26 Oct
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,338 reviews)
It was ok

Reviewed on 21 Sept 2026

Don't see what you're looking for?
See all available trips from London to Southern Wisconsin
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How to find a romantic Southern Wisconsin holiday

How can I find the best Southern Wisconsin vacation packages for couples?

Use our easy-to-use holiday search tools to plan your most-romantic getaway to Southern Wisconsin. Choose a hotel suite with an on-trend bathtub with a big view. Choose a stylish hire car with the top down to woo your heart. Choose candlelit cocktails on the shoreline, a horse ride by moonlight or a dolled-up night at the casino.

Can I book cheap Southern Wisconsin romantic holidays for two?

Get wallet-friendly away-from-it-all romantic accommodation at Expedia, so you have more kitty to spend on romantic activities. We have cheap romantic holidays to Southern Wisconsin that start from £890. Prices and availability are subject to change. Additional terms may apply.

What should I think about when booking a Southern Wisconsin romantic getaway?

The most romantic holidays are about building memories, about dancing and dining and keeping the spark alive. These are moments to level up the luxury – use the star filter to find the best of the best, maybe even tick the business-class flights filter to make the journey part of the adventure.

What should I look for in a luxury romantic holiday to Southern Wisconsin?

Spoil yourselves with a few luxuries on your romantic trip away. You can use our filters to add that extra touch of romance to your holiday: glamorous spas, divine private dining, exquisite room service.

Can I book a romantic hot-tub holiday in Southern Wisconsin?

What’s more romantic than a hot tub under the stars, together? Add a glass of fizz, a gorgeous view and Cupid’s arrow and you’re good. To find accommodation with bubbles, use our dedicated hot-tub filter.

How can I find romantic holidays for couples in Southern Wisconsin that are all inclusive?

Enjoying an all-inclusive holiday means you can really indulge your appetites together – with the promise of no awkward arguments about splitting the bill. Simply use our all-inclusive filter to see what romantic options are available.

Can I book a romantic trip to Southern Wisconsin with free cancellation and/or flexible dates?

Even the best laid plans fall through sometimes. Make sure you’re not caught out – using our filters to find free cancellation accommodation. Just make sure you check the all-important small print.

Why should I book my Southern Wisconsin romantic holiday with Expedia?

At Expedia, we know the not-so-secret ingredients to the perfect romantic holiday. Our handy filters help you search a huge range of options and book a holiday that gets your hearts racing.

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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.