Townhome vacation rentals in Downtown Chicago

Find and book unique townhouses on Airbnb

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Popular amenities for Downtown Chicago townhouses

Family-friendly townhouses

Guest favourite
Townhouse in Chicago
4.96 out of 5 average rating, 69 reviews

Beautiful Spacious RiverWest Townhome 4-Bed/4-Bath

KayRating, 5 stars7 months ago
If you stay at Cary's place (and you should!), be sure to ask him for restaurant recommendations! He knows these restaurants, knows the owners, and even knows what some of their specialties are! This condo is amazing and we will be staying again.
Guest favourite
Townhouse in Chicago
4.85 out of 5 average rating, 167 reviews

Downtown Elegance ✨ Private Yard Parking

KatieRating, 5 stars1 month ago
Alexandra was really prompt with responses and super helpful before our stay! The location was fabbbb!!! We would stay here again!
Guest favourite
Private room in Chicago
4.83 out of 5 average rating, 138 reviews

Private Bedroom w/ bath in Chicago Downtown/Loop

NoelleRating, 5 stars5 months ago
Great location, would stay again. Very walkable to metro station and Fulton Market. Place was quiet and safe. Easy access instructions, simple to follow. Host was very clear with instructions and responsive.
Guest favourite
Townhouse in Chicago
4.87 out of 5 average rating, 346 reviews

CITY CONDO with GARAGE 7 min Walk to Train

RickRating, 5 stars3 days ago
The host is very communicative and helpful. Very nice to have a garage space for the car while visiting Chicago. The neighborhood is quiet and easy to access from the city. Would definitely book again!
Guest favourite
Private room in Bolingbrook
4.8 out of 5 average rating, 83 reviews

Cozy basement with private Bathroom

MingiRating, 5 stars2 months ago
I stayed here for 3 months to visit Argonne National Laboratory, and it was the perfect place to stay! Supermarkets such as Walmart, Meijer, Tony's and many chain restaurants are around a few minutes away by a car. It takes around 10 mins to get to the Argonne Lab. If you're planning to visit the Argonne Lab, this could be your best choice :) Although it's half-basement, the place is so spacious, so I'm 100% sure it would be better than just living in other small Airbnb rooms. Rose is really understandable easy going person, and she always respect my privacy! And if something happens, don't worry she's gonna text you back so quickly There's a cute dog named Lucy, she is really adorable. If you're a pet lover, you must like it!
Top guest favourite
Private room in Chicago
4.96 out of 5 average rating, 236 reviews

Spacious garden level suite

ChristianeRating, 5 stars1 month ago
I know people read the latest reviews, so I am always writing the same thing. Petra's place is a gem, my favorite in Chicago (I have to come to work 6 times a year). It is extremely clean and confortable, you have 2 very spacious rooms, closet and drawers to unpack, nice bed. No kitchen, but you can microwave meals and the restaurants in Roscoe Village are great. Bus nearby and Metro 15mn walk.
Townhouse in Chicago
4.6 out of 5 average rating, 194 reviews

Chicago’s Dickens Place a trendy centralized flat

RaineRating, 5 stars3 months ago
My partner and I were visiting Chicago to celebrate his birthday and stayed here about 2 weeks ago. I'm a very experienced traveler but this was my first time staying in an Airbnb since 2019, and I love the comfortable feeling of being in a home while on the road. This spot was very conveniently placed around Logan Square and the neighborhood felt safe. The host was very helpful, super quick to respond, respectful and gave us tons of itinerary recommendations. 💯 I liked the medieval decor around the apartment. It was very suiting for our trip since we went to Medieval Times Dinner and a dungeon synth show during our stay in Chicago. ⚔️ I will be using Airbnb more often in the future.
Superhost
Private room in Chicago
4.71 out of 5 average rating, 138 reviews

Private Room and Bath in Perfect Location

AustinRating, 5 stars7 months ago
Great location and a great price! Would certainly stay again!

Townhouse rentals with a washer and dryer

Townhouse in Chicago
5 out of 5 average rating, 3 reviews

Chicago West Town Row House

MarthaRating, 5 stars3 months ago
This was very comfortable and perfectly located. Parking was especially helpful. It really is a home, unlike many Airbnb that are investment properties, and you could feel it. Thank you Marie.
Townhouse in Chicago
4.86 out of 5 average rating, 63 reviews

Logan Square Duplex Smart Home w/Garage by 606 Trl

RakiahRating, 5 stars8 months ago
Angie was extremely responsive to my messages before and during my booking. Check-in was easy, and we had everything we needed for our stay. Great home for a group of 4-6 people.
Guest favourite
Townhouse in Chicago
5 out of 5 average rating, 5 reviews

Quiet Townhome, Near Lakefront and Downtown

ArielRating, 5 stars1 week ago
Brandon home was amazing it was nice and clean and the rooms was big
Guest favourite
Townhouse in Chicago
4.86 out of 5 average rating, 104 reviews

Modern Downtown Home with 5 Baths & Private Garage

SummerRating, 5 stars4 months ago
We had a great stay and enjoyed the apartment!
Guest favourite
Townhouse in Des Plaines
4.98 out of 5 average rating, 83 reviews

Upscale 3 bed 1.5 bath near Chicago O'Hare Airport

TrishaRating, 5 stars3 days ago
Habeeba is a great host and goes above and beyond to make sure you feel at home. The location and townhouse was perfect for our short trip to visit family.
Townhouse in Chicago
4.67 out of 5 average rating, 3 reviews

Beautiful & Spacious Family Friendly Town House

JoshuaRating, 5 stars8 months ago
We had an amazing stay at this property in Chicago! The home was even better than the photos, offering plenty of space for our group of six, with room to spare. The layout was perfect, with lots of bathrooms and large windows that filled the space with natural light. The real plants throughout the house added a lovely touch. The location was ideal, within walking distance to grocery stores and fantastic restaurants right next door. We celebrated my husband's 40th birthday weekend here, and it was the perfect setting for our special occasion. Our host, Alice, was incredibly attentive, checking in with us throughout our stay and providing extra supplies when needed. Her hospitality made our experience even more enjoyable. I highly recommend this home to anyone looking for a comfortable and convenient place to stay in Chicago. We couldn’t have asked for a better place to celebrate and enjoy the city!
Townhouse in Chicago
4.67 out of 5 average rating, 3 reviews

Vital Urban: Spa Inspired Retreat

EdRating, 5 stars3 weeks ago
Rain’s place was nothing short of awesome!! My boys said it was their dream home! The location was ideal - walking distance to all the best eateries, shopping and public transportation.
Guest favourite
Townhouse in Chicago
4.89 out of 5 average rating, 91 reviews

Sanitized Home, 4BR/3BA, Free Parking available

ZoeyRating, 5 stars1 week ago
Karen was a great host and the home was a great stay. Almost everything is on a separate floor, so there's a half-staircase to get to the kitchen and the living room, etc. This was not a problem for a group though. The only issue that we had was that the parking spot listed that goes behind the garage could not fit a majority of cars. I believe the spot would fit about a smart car and cars of similar size. But the free parking across the street was available the majority of the weekend, so it wasn't a problem.

Townhouses with an outdoor patio

Guest favourite
Townhouse in Oak Park
4.94 out of 5 average rating, 16 reviews

A Pleasant Stay in Oak Park

TimothyRating, 5 stars3 weeks ago
We found Jay's place to be an excellent value: great location close to public transportation & within walking distance of good restaurants (& a terrific Italian bakery). The kitchen amenities were excellent, & the whole place seemed to have been renovated recently. We'd definitely stay there again when visiting Chicago.
Superhost
Townhouse in Evanston
4.81 out of 5 average rating, 58 reviews

Charming 2 bedrooms in the Evanston art district

Mary BethRating, 5 stars1 month ago
Celina’s apartment was as pictured. We enjoyed having the fireplace while watching tv. Big plus was that we never had to search for parking! Its location was perfect to get to many places with ease.
Guest favourite
Townhouse in Chicago
4.93 out of 5 average rating, 28 reviews

3-Story,Free Parking,No Pet Fee,Private Patio,W/D

HeatherRating, 5 stars2 weeks ago
We loved our stay! Great location. Beautiful area. Felt very safe. Easy to find and park. Emily provided street parking passes for our second car. We walked everywhere or took the train. When we had a question at check in they answered right away and were very helpful. We travelled with teens, dogs, and grandparents. This is a perfect place for dogs! Great patio, comfy beds, dog bed and bowls, and most importantly next to many parks for the dogs. The kitchen had everything we needed. There is a grocery store, Starbucks, and Target down the street. Kids figured out the TV right away. Considerations when booking: this is a three story house with the bedrooms and shower upstairs, laundry downstairs and the stairs are spiral staircases. No biggie for us but if you have mobility concerns (human or dog) this might prove challenging. The water pressure in the shower was low but plenty of hot water for all of us. We would definitely come again! Thanks Emily!
Superhost
Townhouse in Chicago
4.77 out of 5 average rating, 66 reviews

Charming & Comfy Gem ~ 10 Mins to Downtown ~Patio!

Galen HowardRating, 5 stars1 month ago
Awesome place! Very safe and very well located with a great amount of restaurants and breweries near by!
Superhost
Townhouse in Chicago
4.77 out of 5 average rating, 13 reviews

Lux Full House: Outdoor Paradise + FREE Parking!

EmmaRating, 5 stars6 months ago
We loved this home away from home for our family. Thank you for opening up your well designed home for us. The location is perfect - quiet enough but near Wicker happenings & grocery etc. The hosts were very helpful, responsive, gracious when we messed a couple things up. We really appreciate such a great stay. My only small qualm is the lack of new/clean/working high end appliances we would ordinarily find in a home of this cost. However we booked last minute and didn’t specifically request anything. And found everything we needed to do the job. I highly recommend this Airbnb stay!
Top guest favourite
Townhouse in Winnetka
4.95 out of 5 average rating, 41 reviews

Warm and Cheerful 3 Bedroom Winnetka Townhouse

RosemaryRating, 5 stars3 weeks ago
This was our fifth stay at Gabriel and Glaucia's property. We love coming to this property because it is comfortable, inviting, and allows each of us space to work and relax. The kitchen is outfitted well for cooking. Their property is always immaculate, and Gabriel is quick to respond to any questions. It is in a most convenient location. Having a garage is especially convenient. Highly recommended ~ and we'll definitely come back!
Guest favourite
Townhouse in Elmhurst
4.91 out of 5 average rating, 70 reviews

Full TownHouse 7.6 miles O'Hare

EricaRating, 5 stars1 month ago
This home was a nice little retreat away for the weekend. She left small puzzles and drawing game out for my kids along with a small packet of treats for our dog as a welcome! There are also games and books for the family to enjoy. The home felt very cozy and comfortable. The fenced in yard was great for our dog. Highly recommend!
Top guest favourite
Townhouse in Chicago
4.99 out of 5 average rating, 75 reviews

𓃥Wicker Cozy Corner w/Parking on site

SairaRating, 5 stars1 week ago
Incredible stay! Hien was so friendly and responsive, the unit was beautiful and felt more spacious in person than in the photos! Lovely spot in the neighborhood, quiet street and amazing food and things to do nearby. Thanks so much Hien!

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