West Side Romantic Holidays
Book a Romantic Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
Top flight + Romantic hotel deals in West Side
Hotel Felix River North/Magnificent Mile
Reviewed on 14 Aug 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Reviewed on 14 Aug 2026
5* Romantic holidays in West Side
4 Night Romantic holidays in West Side
How to find a romantic West Side holiday
How can I find the best West Side vacation packages for couples?
Use our easy-to-use holiday search tools to plan your most-romantic getaway to West Side. 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 West Side 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 West Side that start from £1,018. Prices and availability are subject to change. Additional terms may apply.
What should I think about when booking a West Side 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 West Side?
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 West Side?
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 West Side 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 West Side 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 West Side 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.
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
Chicago: Navy Pier Centennial Wheel Ticket
Top Romantic Holiday Destinations
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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.
