Find Romantic Hotels in Old Town Chicago, IL

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Old Town Chicago Romantic Hotels

Top Old Town Chicago Romantic Hotels

Hotel Lincoln

4.0 star property
Lincoln Park
7.8 out of 10, Good, (1044)
"Great location and friendly staff!"
United States
Evan
The price is NT$3,065
NT$4,148 total
includes taxes & fees
Dec 7 - Dec 8
Hotel Lincoln

Hilton Chicago/Magnificent Mile Suites

3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3340)
"Great stay!"
United States
Rose
The price is NT$2,603
NT$3,055 total
includes taxes & fees
Dec 7 - Dec 8
Hilton Chicago/Magnificent Mile Suites

Warwick Allerton - Chicago

4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (3000)
"Beautiful hotel, very well situated near restaurants shopping and mass transit "
United States
Joan
The price is NT$1,999
NT$3,263 total
includes taxes & fees
Dec 15 - Dec 16
Warwick Allerton - Chicago

Embassy Suites by Hilton Chicago Downtown River North

4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (5278)
"Nice staff A lot of restaurants and stores near the hotel Good breakfast "
United States
Viviana Velazquez
The price is NT$2,723
NT$3,197 total
includes taxes & fees
Dec 21 - Dec 22
Embassy Suites by Hilton Chicago Downtown River North

Swissotel - Chicago

4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (2964)
"Great stay"
Canada
Lorrington Ashford
The price is NT$2,736
NT$4,129 total
includes taxes & fees
Dec 14 - Dec 15
Swissotel - Chicago

Silversmith Hotel Chicago Downtown

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2077)
"Lovely hotel in a great spot!"
United States
Natasha
Silversmith Hotel Chicago Downtown

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2240)
"Room was spotless…staff was great!"
United States
Tamika
The price is NT$2,689
NT$4,220 total
includes taxes & fees
Dec 16 - Dec 17
Sable at Navy Pier Chicago, Curio Collection by Hilton

The Royal Sonesta Chicago Downtown

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3073)
"Great stay Great staff Would love to stay again when I come back"
United States
Stephanie A
The price is NT$3,560
NT$5,179 total
includes taxes & fees
Dec 22 - Dec 23
The Royal Sonesta Chicago Downtown

Courtyard by Marriott Chicago Magnificent Mile

3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1560)
"Great hotel and nice "
Canada
Anthony
The price is NT$3,054
NT$3,585 total
includes taxes & fees
Dec 18 - Dec 19
Courtyard by Marriott Chicago Magnificent Mile

The Godfrey Hotel Chicago

4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1904)
"Awesome staff and great location "
United States
Luis C
The price is NT$2,603
NT$3,789 total
includes taxes & fees
Nov 24 - Nov 25
The Godfrey Hotel Chicago
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.

Find out more about Old Town Chicago

Old Town Chicago attractions for couples

In Old Town Chicago, travelers will find a captivating blend of history, culture, and vibrant city life. Begin your exploration at the iconic Second City, where you can catch a hilarious improv show that has launched the careers of many famous comedians. Just a short stroll away, the Old Town Arts Fair showcases local artisans and live music, immersing visitors in the community's creative spirit each spring. For a taste of history, visit the Old Town Triangle Historic District, where charming Victorian homes line the streets, offering a glimpse into the neighborhood's past. Families will enjoy a day at the nearby Lincoln Park Zoo, which features free admission and a plethora of engaging animal exhibits perfect for children of all ages. Don't miss the bustling Wells Street, lined with eclectic shops, trendy boutiques, and inviting cafes, perfect for a leisurely afternoon of shopping and dining. When it comes to accommodations, hotels in Old Town cater to the Quality Seeker with spacious rooms, modern amenities, and attentive service, ensuring a pampered stay. Imagine winding down at a chic rooftop bar with stunning views of the Chicago skyline after a day of adventures, all while knowing that your family is well taken care of in a vibrant neighborhood rich with experience.

Top Old Town Chicago Hotel Reviews

Explore a world of travel with Expedia

Frequently asked questions

Searching for romantic hotels in Old Town Chicago?
If you and your partner need a romantic vacation, we've got just the ticket. Our guests also love Old Town Chicago for its bar scene, array of dining options, and cozy coffeehouses. If you want to explore the area, you might head to Second City, Armitage Avenue, or Henry Gerber House. If you're interested in staying near a certain attraction, you can sort by neighborhood or distance to top landmarks, so you and your partner will get to see everything on your list.
What is there to do in Old Town Chicago?
There's nothing better than experiencing a new place with your sweetheart, so consider checking out all there is to see and do in Old Town Chicago. If you and your partner are interested in sampling the local food and drinks, you'll love Old Town Chicago for its bar scene, array of dining options, and cozy coffeehouses. You might think about stopping by Second City, Armitage Avenue, or Henry Gerber House while you're seeing the sights.
What's the best way to get to Old Town Chicago and around town during my romantic getaway?
This information about transportation options in Old Town Chicago might help your romantic getaway go off without a hitch: Fly into Chicago Midway Airport (MDW), which is the closest major airport, located 10 mi (16 km) away. Local metro stations include Sedgwick Station and Clark-Division Station.