Find Romantic Hotels in Old Town Chicago, Chicago from $109

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Check availability on Old Town Chicago Romantic Hotels

Our top choices for Old Town Chicago romantic hotels

Hotel Lincoln

4.0 star property
Lincoln Park
7.8 out of 10, Good, (1060)
"Great "
United States
Lillian
$122 nightly
The price is $143
Dec 17 - Dec 18
Total with taxes and fees
Hotel Lincoln

Silversmith Hotel Chicago Downtown

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2108)
"Great hotel. Very affordable for such a perfect location."
United States
Nicholas
$127 nightly
The price is $149
Jan 4 - Jan 5, 2026
Total with taxes and fees
Silversmith Hotel Chicago Downtown

Eurostars Magnificent Mile

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3155)
"Amazing and will be staying again!"
United States
Angie
$94 nightly
The price is $110
Jan 8 - Jan 9, 2026
Total with taxes and fees
Eurostars Magnificent Mile

The Godfrey Hotel Chicago

4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1916)
"Good value, great cleaning staff "
United Kingdom
farzana
$115 nightly
The price is $135
Jan 6 - Jan 7, 2026
Total with taxes and fees
The Godfrey Hotel Chicago

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

4.0 star property
Downtown Chicago
8.2 out of 10, Very Good, (2748)
"Great food clean room friendly staff"
United States
MARINA
$110 nightly
The price is $129
Jan 6 - Jan 7, 2026
Total with taxes and fees
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Warwick Allerton - Chicago

4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (3008)
"Enjoyed this hotel stay. "
United States
Kimberly
$93 nightly
The price is $109
Dec 22 - Dec 23
Total with taxes and fees
Warwick Allerton - Chicago

Hilton Chicago/Magnificent Mile Suites

3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3459)
"Great place to stay "
United States
RaShawna
$106 nightly
The price is $124
Dec 17 - Dec 18
Total with taxes and fees
Hilton Chicago/Magnificent Mile Suites

Swissotel - Chicago

4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3003)
"Very beautiful place to stay"
United States
FaithBrenda
$139 nightly
The price is $163
Jan 2 - Jan 3, 2026
Total with taxes and fees
Swissotel - Chicago

The Royal Sonesta Chicago Downtown

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3136)
"I loved staying at this hotel! Staff was very nice , I will definitely stay here again."
United States
Stephanie
$141 nightly
The price is $166
Jan 8 - Jan 9, 2026
Total with taxes and fees
The Royal Sonesta Chicago Downtown

LondonHouse Chicago, Curio Collection by Hilton

4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3436)
"Great Hotel!"
United States
Siranush
$130 nightly
The price is $153
Jan 4 - Jan 5, 2026
Total with taxes and fees
LondonHouse Chicago, Curio Collection by Hilton
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

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.

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