
Places to stay in Old Town, Chicago
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Top-rated places to stay in Old Town, Chicago
Guests agree: these places to stay are highly rated for location, cleanliness, and more.
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Popular amenities for Old Town, Chicago places to stay
Other great vacation rentals in Old Town, Chicago
Top guest favorite

Guesthouse in Wicker Park
4.98 out of 5 average rating, 42 reviewsSolar Victorian MCM Coach House
AsitRating, 5 stars1 week ago
We had a lovely stay at this quiet little oasis in Wicker Park. The Coach House is charming, comfy, spotless, and stocked with everything you need. There is great food and transit just steps away. Joe and Shannon are fantastic hosts—friendly, responsive, and full of great local tips. You can tell they really love their city, and it shows in the way they host. Can’t wait to come back!
Guest favorite

Apartment in Lincoln Park
4.92 out of 5 average rating, 38 reviewsLincoln park getaway, Outdoor patio! Summer Fun!
ErinRating, 5 stars3 weeks ago
Fantastic location. Beautiful neighborhood, street parking was easy to find and lots to do within walking distance. Highly recommend!!
Superhost

Condo in Lincoln Park
4.92 out of 5 average rating, 12 reviewsCozy Condo, Sleeps 2!
BriannaRating, 5 stars3 weeks ago
I enjoyed my stay. The neighborhood was walkable and quiet. Check-in went smoothly and there were no issues throughout my stay. Thomas was very communicative and responsive.
Guest favorite

Apartment in Near North Side
4.92 out of 5 average rating, 37 reviewsLincoln Park Haven: Balcony, Walk to Whole Foods
HoustonRating, 5 stars1 month ago
We had a great stay at this apartment in Lincoln Park. The view was excellent, and the building amenities were a nice bonus. The location was convenient too--Whole Foods was right across the street, with other shops like REI nearby. It was easy to get downtown and explore other parts of Lincoln Park. We were traveling with a toddler and a newborn, and the host helped by providing a pack 'n play. Communication was clear and timely. Overall, a smooth experience.
Superhost

Apartment in Old Town
4.88 out of 5 average rating, 8 reviewsComfortable & Modern Studio in City Center 1 Bath
EllaRating, 5 stars3 weeks ago
Stayed here for a few nights to explore Chicago, the location and the apartment were amazing! TJ and Hatice were super easy to contact and were super accommodating:)
Top guest favorite

Condo in Old Town
4.98 out of 5 average rating, 64 reviewsTwo Floor Luxury 3 Bedroom Condo in Old Town
BetsyRating, 5 stars3 weeks ago
What a gem - We loved our stay! Whenever you find a beautiful, comfortable, well appointed home in a GREAT location with a helpful, kind and responsive host it’s a huge win! This stay checked all of those boxes and will most definitely be on our ‘repeat properties’ list.
Guest favorite

Home in Lincoln Park
4.98 out of 5 average rating, 80 reviewsOpulent 3bdr2bth Old Town Luxury + Parking prmts
MehganRating, 5 stars3 weeks ago
Lovely space and a perfect location for exploring the city. Great restaurants within a short walk. Lincoln Park also just a short walk.
Superhost

Condo in Old Town
4.88 out of 5 average rating, 90 reviewsSpacious & Elegant Old Town Duplex
AmyRating, 5 stars1 week ago
This condo worked great for our family of 5 (3 teenagers). The location was ideal to the train and bus stops. We were able to easily walk to Old Town where we enjoyed Second City, Corcoran’s Pub and Jeni’s Ice Cream. We felt the condo was in a safe location. You can hear the L go by, but we didn’t mind it; reminded me we were in the city. We were able to secure a parking spot (SpotHero) right behind the condo which was ideal. Was it a bit pricey, yes…it’s Chicago, everything was expensive. Enjoyed our visit!
Quick stats about vacation rentals in Old Town, Chicago
Total rentals
80 properties
Nightly prices starting at
G$14,640 GYD before taxes and fees
Total number of reviews
6.8K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Wicker Park
- Illinois Beach State Park
- Brookfield Zoo
- Washington Park Zoo
- The 606
- The Beverly Country Club
- Flossmoor Golf Club