Illinois Romantic Vacations

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

Top Romantic vacation packages in Illinois

Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
Pendry Chicago
Trump International Hotel & Tower Chicago
LondonHouse Chicago, Curio Collection by Hilton
Omni Chicago Hotel
Don't see what you're looking for?
See all available trips from Columbus to Illinois
View all trips

5* Romantic vacations in Illinois

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Waldorf Astoria Chicago
The Peninsula Chicago
Don't see what you're looking for?
See all available trips from Columbus to Illinois
View all trips

3 Night Romantic vacations in Illinois

Price found within the past 48 hours. Click for updated prices.
The Drake
Pendry Chicago
LondonHouse Chicago, Curio Collection by Hilton
Don't see what you're looking for?
See all available trips from Columbus to Illinois
View all trips

4 Night Romantic vacations in Illinois

Price found within the past 48 hours. Click for updated prices.
Eurostars Magnificent Mile
LondonHouse Chicago, Curio Collection by Hilton
Fairmont Chicago at Millennium Park
Don't see what you're looking for?
See all available trips from Columbus to Illinois
View all trips

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

How to find a romantic Illinois vacation

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

To win over the love of your life, first choose where and when you want to bring the romance. Now flirt with the filters to add ocean views, spa, pools, and anything else that gets your heart racing.

How can I find cheap Illinois romantic packages for two?

For dollar-friendly delights, sort your search results by price or deals. You can also filter by budget to find romantic retreats at prices you’ll love. For an affordable and alluring adventure, try self-catering.

How can I plan a great romantic trip to Illinois?

Find what fills you with joy and dive right in, whether you thrill in a little adventure or lust for long lazy days by the pool, handcrafted cocktails in hand. Fire cupid’s arrow at our filters and build your dream trip for two.

How much is a trip for two to Illinois?

Put a price on love with stunning deals for duos starting at just $266. Prices and availability are subject to change. Additional terms may apply.

Can I book Illinois spa packages for couples?

Check the filter box for a seductive stay at a spa. Sort your results by price, deals, rating, and more to guarantee the perfect match.

How can I book romantic weekend getaway packages in Illinois?

To book a loved-up break in Illinois, enter your travel dates and sort by price, deals, rating—whatever matters most to you and your partner. Now, you can add some adult-only amenities, like a hot tub or full-service spa for total R, R, & R (that’s romance, rest, and recuperation).

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

The course of true love should always run smooth, but we get that there are hiccups. So, filter by payment option to search for romantic stays with free cancellation and buy now, pay later options.

Why should I book my Illinois romantic holiday with Expedia?

If you’ve only got eyes for excellent escapes, book your loved-up break with Expedia. Fling the filters to find accommodation you’ll adore. And what’s more attractive than ATOL protection?

Top Romantic Illinois Hotels

The Champagne Lodge & Luxury Suites

The Champagne Lodge & Luxury Suites

3.5 out of 5
16 W 621 S. Frontage Rd Willowbrook IL
  • 44 min drive from Wrigley Field
$112 nightly
The price is $117 total per night from Mar 4 to Mar 5
$117 total
Mar 4 - Mar 5
Total with taxes and fees
For a romantic stay, consider this boutique hotel, featuring a garden, jetted tubs, and in-room fireplaces. Couples will appreciate the romance packages and ...
8.6/10 Excellent! (1,426 reviews)

Couples like: adults only property, spa tub, fireplace, romance packages available

Travelers say...
The room had a weird smell…

Reviewed on Mar 1, 2026

The Champagne Lodge & Luxury Suites
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
85 East Wacker Drive Chicago IL
  • 10 min drive from Wrigley Field
$229 nightly
The price is $269 total per night from Mar 16 to Mar 17
$269 total
Mar 16 - Mar 17
Total with taxes and fees
Indulge in a romantic getaway at this upscale hotel, where you'll find a spa, in-room massages, and onsite dining. Couples will love the Frette Italian sheets ...
9.4/10 Exceptional! (3,608 reviews)

Couples like: full-service spa, couples spa treatments, bar

Travelers say...
spotless room, comfortable bed, and fantastic view!!!

Reviewed on Mar 2, 2026

LondonHouse Chicago, Curio Collection by Hilton
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
  • 12 min drive from Wrigley Field
$157 nightly
The price is $180 total per night from Apr 1 to Apr 2
$180 total
Apr 1 - Apr 2
Total with taxes and fees
You and your special someone are sure to love the
8.6/10 Excellent! (2,311 reviews)

Couples like: full-service spa, couples spa treatments, happy hour

Travelers say...
Couldn’t ask for better service and hospitality. Only wish is that the tub was larger, but it is standard sized

Reviewed on Mar 2, 2026

Palmer House a Hilton Hotel
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 vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.