Illinois Romantic Vacations

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Top Romantic vacation packages in Illinois

Price found within the past 48 hours. Click for updated prices.
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

Downtown Chicago
$562
per person
Nov 7 - Nov 10
found 20 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
9.2/10 Wonderful! (1,407 reviews)
Amazing staff— amazing location and amenities— easy to get around — good late night dining options within walking distance

Reviewed on Sep 7, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
$813
per person
Nov 7 - Nov 9
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Chicago (ORD)
9.6/10 Exceptional! (2,003 reviews)
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

Downtown Chicago
$643
per person
Nov 8 - Nov 11
found 1 hour ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9/10 Wonderful! (1,123 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
Save 100% on your flight
$1,155
per person
Nov 7 - Nov 9
found 16 hours ago
Roundtrip non-stop flight included
New York (NYC) to Chicago (ORD)
9.8/10 Exceptional! (1,013 reviews)
I liked everything about this

Reviewed on Sep 6, 2026

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

Downtown Chicago
Save 100% on your flight
$1,022
per person
Oct 7 - Oct 10
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
9/10 Wonderful! (1,119 reviews)
Wonderful location and friendly staff. Rooms were clean and spacious. I would definitely stay here again.

Reviewed on Sep 6, 2026

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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

Trump International Hotel & Tower Chicago

Downtown Chicago
$813
per person
Nov 7 - Nov 9
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Chicago (ORD)
9.6/10 Exceptional! (2,003 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
Save 100% on your flight
$1,155
per person
Nov 7 - Nov 9
found 16 hours ago
Roundtrip non-stop flight included
New York (NYC) to Chicago (ORD)
9.8/10 Exceptional! (1,013 reviews)
I liked everything about this

Reviewed on Sep 6, 2026

The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

Downtown Chicago
Save 100% on your flight
$2,416
per person
Oct 8 - Oct 10
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
9.2/10 Wonderful! (1,004 reviews)
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3 Night Romantic vacations in Illinois

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

Pendry Chicago

Downtown Chicago
Save 100% on your flight
$525
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.2/10 Wonderful! (1,162 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
$892
per person
Nov 7 - Nov 10
found 20 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
9.6/10 Exceptional! (2,003 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
Save 100% on your flight
$664
per person
Nov 7 - Nov 10
found 20 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
The hotel was perfectly fine for a room price half the cost we paid

Reviewed on Sep 6, 2026

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4 Night Romantic vacations in Illinois

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

Swissotel - Chicago

Downtown Chicago
Save 100% on your flight
$844
per person
Nov 7 - Nov 11
found 21 hours ago
Roundtrip non-stop flight included
New York (NYC) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
The hotel was perfectly fine for a room price half the cost we paid

Reviewed on Sep 6, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
$1,136
per person
Nov 7 - Nov 11
found 21 hours ago
Roundtrip non-stop flight included
New York (NYC) to Chicago (ORD)
9.6/10 Exceptional! (2,003 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
Save 100% on your flight
$1,724
per person
Nov 7 - Nov 11
found 21 hours ago
Roundtrip non-stop flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
The rooms need to be updated. The room service and bell man took longer than we expected for a Four Seasons. There needs to be someone right when you walk in to direct new guests. We usually stay at the Peninsula Hotel. We wanted to try the Four Seasons but we will go back to the Peninsula Hotel going forward. We got the same type of suite but the bathroom and closet for a family of four was less than desirable. The bar at the hotel had great service! Great selection of upscale bar food. I was very happy about that service! I will say everyone was pleasant and accommodating! The wait times and the lack of attention for need to be compared to the Peninsula.

Reviewed on Sep 7, 2026

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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 $525. 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

16 W 621 S. Frontage Rd Willowbrook IL
  • 44 min drive from Wrigley Field
$139 nightly
$146 total
Sep 8 - Sep 9
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 ...
The Champagne Lodge & Luxury Suites
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

85 East Wacker Drive Chicago IL
  • 11 min drive from Wrigley Field
$300 nightly
$357 total
Sep 20 - Sep 21
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 ...
LondonHouse Chicago, Curio Collection by Hilton
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

17 E Monroe St Chicago IL
  • 12 min drive from Wrigley Field
$278 nightly
$331 total
Sep 9 - Sep 10
Total with taxes and fees
You and your special someone are sure to love the
Palmer House a Hilton Hotel
See all 10,381 properties in Illinois
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.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$27
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

$47
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Flyover in Chicago

Flyover in Chicago

$28
per adult
96% of travellers recommend
Flyover in Chicago
See all activities in Illinois

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.