Illinois Romantic Vacations
Book a Romantic Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 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 easyPlan, book, and manage your trip all in one place
Top Romantic vacation packages in Illinois
Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Save 100% on your flight
Price was $678, price is now $450 per person
$450
per person
Jun 11 - Jun 14
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (2,471 reviews)
Staff was friendly, however I asked to have blankets brought up to room two times (one phone call and one text) and there was no follow through. The room smelled like stale smoke. The pull out bed was awful and you could feels the bedsprings. They also offered to bring coffee to the room and when I requested a time, it was never delivered. I mentioned to from desk and they apologized and had coffee sent to room, however we were ready to check out. They did offer a late check out and staff was friendly. We were dissapointed that we couldn't pay cash, although that wouldn't have been a deal breaker. Rooms could use a little updating.
Reviewed on Apr 4, 2026
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,039, price is now $663 per person
$663
per person
Jun 11 - Jun 14
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,123 reviews)
The staff at the Pendry are top notch. We arrived early and just wanted to drop our bags off, but the staff was able to check us in several hours early. Upon learning it was my birthday, the bell hop brought me a glass of wine from the bar and later, the staff sent up a bottle of prosecco and birthday cupcakes. Our room
Reviewed on Apr 7, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $892, price is now $641 per person
$641
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
9.4/10 Exceptional! (3,647 reviews)
London House is in the perfect location directly across from the Chicago Riverwalk with easy walking access to many of the tourist attractions. Staff were so friendly and helpful! We thoroughly enjoyed our stay and plan to visit again.
Reviewed on Apr 10, 2026
Omni Chicago Hotel
Downtown Chicago
Save 100% on your flight
Price was $857, price is now $618 per person
$618
per person
May 12 - May 15
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
9.2/10 Wonderful! (1,720 reviews)
The staff was amazing, i’ve stayed at omni all over the country, the room was spacious. The only complaint is that the rooms are super dated and you can tell they haven’t been renovated in a while so there’s a lot of visible wear and tear on everything. The sliding door to the bathroom was broken and the shower drain got clogged during stay so the tub was filling up while you’re in the shower. just little things like that, we didn’t spend much time in the room so it was fine and the staff was amazing just don’t expect the state of the art room.
Reviewed on Apr 10, 2026
5* Romantic vacations in Illinois
Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,190, price is now $1,036 per person
$1,036
per person
Jun 11 - Jun 14
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Beautiful and in walking distance to so many shops and cafes! We had a great stay.
Reviewed on Apr 6, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was $1,408, price is now $1,037 per person
$1,037
per person
Jun 11 - Jun 14
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
Beautiful facility, excellent service, professional staff, delicious food!
Reviewed on Apr 7, 2026
Waldorf Astoria Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,687, price is now $1,287 per person
$1,287
per person
Jun 11 - Jun 14
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Top of the line customer service! I can’t express how deeply I am impressed with your hotel, the feel, the specialness of it all! My first time there, has left me with a lasting impression I will never forget! Classy and it smelled like Paris! Love everything about the hotel. Wish I could have stayed longer. Thank you for keeping such a prestigious hotel at top standard!
Reviewed on Apr 6, 2026
3 Night Romantic vacations in Illinois
Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Save 100% on your flight
Price was $678, price is now $450 per person
$450
per person
Jun 11 - Jun 14
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (2,471 reviews)
Staff was friendly, however I asked to have blankets brought up to room two times (one phone call and one text) and there was no follow through. The room smelled like stale smoke. The pull out bed was awful and you could feels the bedsprings. They also offered to bring coffee to the room and when I requested a time, it was never delivered. I mentioned to from desk and they apologized and had coffee sent to room, however we were ready to check out. They did offer a late check out and staff was friendly. We were dissapointed that we couldn't pay cash, although that wouldn't have been a deal breaker. Rooms could use a little updating.
Reviewed on Apr 4, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
Price was $776, price is now $485 per person
$485
per person
May 12 - May 15
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
It was too cold for the pool!
The property is in a great location, the staff kind and very helpful. The on site restaurant is quite wonderful. I would have to say we had the best meal of our stay of 4 nights in Chicago!the rooms are large and airy and very clran
Reviewed on Apr 7, 2026
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,039, price is now $663 per person
$663
per person
Jun 11 - Jun 14
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,123 reviews)
The staff at the Pendry are top notch. We arrived early and just wanted to drop our bags off, but the staff was able to check us in several hours early. Upon learning it was my birthday, the bell hop brought me a glass of wine from the bar and later, the staff sent up a bottle of prosecco and birthday cupcakes. Our room
Reviewed on Apr 7, 2026
4 Night Romantic vacations in Illinois
Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
Price was $1,380, price is now $806 per person
$806
per person
Jun 16 - Jun 20
found 4 hours ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
It was too cold for the pool!
The property is in a great location, the staff kind and very helpful. The on site restaurant is quite wonderful. I would have to say we had the best meal of our stay of 4 nights in Chicago!the rooms are large and airy and very clran
Reviewed on Apr 7, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,682, price is now $1,059 per person
$1,059
per person
Jun 16 - Jun 20
found 4 hours ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
9.4/10 Exceptional! (3,647 reviews)
London House is in the perfect location directly across from the Chicago Riverwalk with easy walking access to many of the tourist attractions. Staff were so friendly and helpful! We thoroughly enjoyed our stay and plan to visit again.
Reviewed on Apr 10, 2026
Thompson Chicago, by Hyatt
Downtown Chicago
Price was $1,786, price is now $1,202 per person
$1,202
per person
Jun 17 - Jun 21
found 20 hours ago
Roundtrip non-stop flight included
Nashville (BNA) to Chicago (ORD)
9.2/10 Wonderful! (1,332 reviews)
Restaurant next door can be loud and surprise you when entering the lobby. Great location. Will return.
Reviewed on Apr 8, 2026
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 $450. 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
16 W 621 S. Frontage Rd Willowbrook IL
$137 nightly
The price is $144 total per night from May 4 to May 5
$144 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! (1,462 reviews)
Couples like: adults only property, spa tub, fireplace, romance packages available
Travelers say...
Great place
Reviewed on Apr 10, 2026
LondonHouse Chicago, Curio Collection by Hilton
85 East Wacker Drive Chicago IL
$270 nightly
The price is $317 total per night from May 11 to May 12
$317 total
May 11 - May 12
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! (3,650 reviews)
Couples like: full-service spa, couples spa treatments, bar
Travelers say...
London House is in the perfect location directly across from the Chicago Riverwalk with easy walking access to many of the tourist attractions. Staff were so friendly and helpful! We thoroughly enjoyed our stay and plan to visit again.
Reviewed on Apr 10, 2026
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
$184 nightly
The price is $212 total per night from May 9 to May 10
$212 total
May 9 - May 10
Total with taxes and fees
You and your special someone are sure to love the
8.6/10 Excellent! (2,375 reviews)
Couples like: full-service spa, couples spa treatments, happy hour
Travelers say...
Very cool historical hotel,
Reviewed on Apr 10, 2026
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.
