Find Romantic Hotels in Old Town Chicago, IL

  • 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

Our top choices for Old Town Chicago romantic hotels

The Den Hotel

The Den Hotel
2.0 star property
Lakeview
8.8 out of 10, Excellent, (28 reviews)
"Great location easy check in nice facilities "
United States
Nicholas
The price is NT$5,136
NT$6,030 total
includes taxes & fees
Mar 29 - Mar 30
The Den 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.

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.

Explore a world of travel with Expedia