Places to stay in Old Town, Chicago

Book unique places to stay, houses, and more on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Old Town, Chicago places to stay

Stay near Old Town, Chicago's top sights

Lincoln Park Zoo1,117 locals recommend
Magnificent Mile598 locals recommend
Pequod's Pizza536 locals recommend
Museum Of Contemporary Art Chicago532 locals recommend
The Signature Room at the 95th®521 locals recommend
Lou Malnati's Pizzeria512 locals recommend

Other great vacation rentals in Old Town, Chicago

Superhost
Home in West Lawn
4.92 out of 5 average rating, 39 reviews

Family Friendly Duplex/9 min from MDW/Free Parking

JoannaRating, 5 stars2 weeks ago
Came for c2e2 with my friends and it was perfect for all of us! Would recommend 💗💗
Guest favorite
Apartment in West Town
4.85 out of 5 average rating, 130 reviews

Condo with private terrace, free WIFI and parking

OlesyaRating, 5 stars3 weeks ago
The place looked much better than on the pictures! It has rooftop patio, spacious, clean, with a unique interior design (vintage). It had plenty of towels, dishes, comforters, so we will definitely come back there when we are in Chicago.
Top guest favorite
Home in Avondale
5 out of 5 average rating, 12 reviews

Alluring Avondale Abode

MichaelRating, 5 stars2 weeks ago
Beth’s home was perfect for our group trip, which centered around cooking together for a Passover Seder! The kitchen had great appliances and equipment, with the space for many of us to cook at once. The house had everything we needed and we were all comfortable.
Superhost
Guest suite in Lincoln Park
4.78 out of 5 average rating, 9 reviews

The Hidden Beach House

MarshaRating, 5 stars6 days ago
The hidden beach house is a lovely place to stay if you are a couple that just wants to get away from everything or if you are like us my daughter and I who came to town and just basically needed a place to sleep and shower. It’s a very small space but it is Clean and quiet thought it was gonna be two rooms but it was not but it wasn’t the hosts mistake. It was mine because I didn’t read the description correctly. The parking garage is about a block and a half down on the main street and it is $38 per day if you try to park on the street and you don’t have a parking permit the people that do have a permits can have you towed so you can play it safe and just pay for the parking or you tried to park on the street and hope nobody towed your car at your expense. Also, you do share a water heater with the rest of the units so be mindful of when you’re getting up and taking a shower so you don’t have a nice cold shower unless that’s what you prefer. And there is so much to do.
Guest favorite
Apartment in Albany Park
4.86 out of 5 average rating, 42 reviews

Elegant 4Bedroom with Free Parking in Albany Park

MatthewRating, 5 stars2 months ago
Wonderful stay as always, thank you so much!
Superhost
Apartment in Jefferson Park
4.63 out of 5 average rating, 24 reviews

City Gem: Stylish 3BR for Urban Explorers

AnnikaRating, 5 stars1 month ago
Peaceful, felt like home, very spacious and comfortable
Guest favorite
Apartment in West Lake View
4.94 out of 5 average rating, 178 reviews

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

DianeRating, 5 stars3 days ago
Sam’s place was beautiful! We felt right at home. The furniture was comfortable and the kitchen had everything we needed. The location was great. We got a free parking spot right outside of the door. Super convenient. We brought our dogs and it was perfect for them. Lots of places to walk and lots of things to do. It was just a short walk to the train. Sam was very easy to get ahold of and was a great host. I definitely recommend and we will be staying here again.
Top guest favorite
Apartment in Irving Park
4.96 out of 5 average rating, 280 reviews

Spacious 1BR apartment in a central location

GilRating, 5 stars1 month ago
I have stayed in a number of AirBnB‘s throughout the years, this may have been my favorite stay. There is absolutely everything you would need for a comfortable stay. Everything is clean. Alex is a five-star communicator. It is a busy little neighborhood, but the bedroom is toward the back of the apartment. I heard nothing but dead silence at night.

Quick stats about vacation rentals in Old Town, Chicago

  • Total rentals

    80 properties

  • Nightly prices starting at

    ﺩ.ﺇ257 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

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago
  6. Old Town