Illinois Romantic Vacations

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    Save up to $2,000 when you book a flight and hotel together*
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Top Romantic vacation packages in Illinois

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
Swissotel - Chicago
Waldorf Astoria Chicago
Trump International Hotel & Tower Chicago
The Peninsula Chicago
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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
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3 Night Romantic vacations in Illinois

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Pendry Chicago
Waldorf Astoria Chicago
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See all available trips from Columbus to Illinois
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4 Night Romantic vacations in Illinois

Price found within the past 48 hours. Click for updated prices.
LondonHouse Chicago, Curio Collection by Hilton
Swissotel - Chicago
Fairmont Chicago at Millennium Park
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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 $445. 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
$126 nightly
The price is $132 total per night from May 4 to May 5
$132 total
May 4 - May 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! (1,487 reviews)

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

Travelers say...
Nice experience

Reviewed on Apr 28, 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
  • 11 min drive from Wrigley Field
$183 nightly
The price is $218 total per night from May 10 to May 11
$218 total
May 10 - May 11
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! (3,668 reviews)

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

Travelers say...
Great location.

Reviewed on Apr 29, 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
$168 nightly
The price is $195 total per night from May 25 to May 26
$195 total
May 25 - May 26
Total with taxes and fees
You and your special someone are sure to love the
8.6/10 Excellent! (2,419 reviews)

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

Travelers say...
The Palmer House has an elegant charm that you feel as soon as you walk into the main lobby. You just want to sit and admire the beauty of this hotel. I loved the whole experience of my stay. I will definitely be going back to the Palmer House.

Reviewed on Apr 29, 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.