Southwest Illinois Romantic Holidays

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

Photo by Southernmost Illinois Tourism Bureau
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    Better together

    Save up to £335 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Packages with flights are ATOL protected

How to find a romantic Southwest Illinois holiday

How can I find the best Southwest Illinois vacation packages for couples?

Use our easy-to-use holiday search tools to plan your most-romantic getaway to Southwest Illinois. 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 Southwest Illinois 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 Southwest Illinois that start from . Prices and availability are subject to change. Additional terms may apply.

What should I think about when booking a Southwest Illinois 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 Southwest Illinois?

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 Southwest Illinois?

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 Southwest Illinois 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 Southwest Illinois 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 Southwest Illinois 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.

Top Romantic Southwest Illinois Hotels

Cozy Cottage On The Shawnee Hills Wine Trail

Cozy Cottage On The Shawnee Hills Wine Trail

Cobden, IL
  • 26 min drive from Southern Illinois University
Stay at this cottage in Cobden. Enjoy free Wi-Fi, a garden and a pool table. Popular attractions Blue Sky Vineyards and Indian Creek Trail Trailhead are located ...
9.8/10 Exceptional! (158 reviews)

Couples like: Hot tub, fireplace

Travellers say...
"BEAUTIFUL place! We loved all the upgrades. The chickens and cat outside were a cute added touch. We enjoyed the pool table,darts, and hot tub in the evening. The Starbucks state mugs were a perfect touch to our morning coffee on the porch! Close to wineries and not far from Lake of Egypt where we ..."

Reviewed on 27 Jul 2025

Cozy Cottage On The Shawnee Hills Wine Trail
Great Shawnee Wine Trail Cabin in Relaxing Setting

Great Shawnee Wine Trail Cabin in Relaxing Setting

Alto Pass, IL
  • 28 min drive from Southern Illinois University
Stay at this cabin in Alto Pass. Enjoy laundry facilities, patios and cable/satellite TV service. Popular attractions Von Jakob Winery & Brewery and Peachbarn ...
10/10 Exceptional! (40 reviews)
"Everything was great! The property was clean and the experience was amazing. The property is beautiful and we even saw a deer walking around!"

Reviewed on 6 Aug 2025

Great Shawnee Wine Trail Cabin in Relaxing Setting
Relaxing Unique Cave Creek Cabin 2 in Shawnee near Alto Pass and Bald Knob Cross

Relaxing Unique Cave Creek Cabin 2 in Shawnee near Alto Pass and Bald Knob Cross

Alto Pass, IL
  • 28 min drive from Southern Illinois University
Stay at this cabin in Alto Pass. Enjoy laundry facilities, patios and cable/satellite TV service. Popular attractions Von Jakob Winery & Brewery and Peachbarn ...
10/10 Exceptional! (45 reviews)
Amazing cabin nestled in the woods but close to everything!
"We very much enjoyed our weekend stay at this amazing cabin! The hosts thought of every detail. Be ready for a stress free, relaxing stay!"

Reviewed on 9 Jul 2025

Relaxing Unique Cave Creek Cabin 2 in Shawnee near Alto Pass and Bald Knob Cross
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.

More holidays you might like

* 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.