
Kid-friendly holiday rentals in West Loop, Chicago
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Top-rated family-friendly rentals in West Loop, Chicago
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Kid-friendly house rentals

The Red Room
Easy to find, in a quiet neighborhood within walking distance from Midway. Erik's place was clean and comfortable, and he was welcoming and friendly.

Welcoming Evanston Home
Jennifer was a very hospitable host and I had a very pleasant stay. The room was very clean and quiet!

Division St Designer Home In Heart of Wicker Park
I traveled to Chicago for work and had a nice three-day stay here. The Airbnb is in a great location, clean, and well-equipped with thoughtful amenities. I particularly enjoyed the small library!

Egyptian Room - Free Parking, 1 block to CTA
Stayed here for a weekend and got exactly what I needed. All I was looking for was a place to sleep and shower when I wasn’t exploring the city and Ryan’s place provided that. The house is close to 2 bus routes and the green line which makes it worth it to me. Being on the west side can be kind of hit or miss but since I grew up in an urban area, it didn’t phase me much…if you’re more sheltered this might be a sketchy area for you. I will say the gas station near the house after sundown can get a little rowdy…might wanna avoid it after dark. To my black folks there are no wash cloths, but body towels are provided. I personally brought my own set of towels [there is a dollar store a couple of blocks away so if you need to just go buy washcloths you can do that]. I loved how dark it got in the room at night so if you like blackout curtains to sleep, this is the perfect room. My only con is the amount of messages you get once your booking starts. Maybe a printout might be better option.

Chicago River House -BBQ Oasis now open!
Even more spacious than in the photos! Well-kept place, with a fully stocked kitchen, projector, BOSE speaker, and great backyard. Double shower in the master bedroom, and strong water pressure. Entry is easy with a code. Finally, the host is VERY accommodating, flexible, and responsive. Recommended!

Gorgeous home, 3BR/2BA, Free Parking, Free Laundry
Samantha’s place is beautiful, well designed, modern, clean and it was very easy to find street parking near house. There are 3 bedrooms, the third bedroom is cabinet only, no bed there. But in one room there is a king bed for 3 people, and second bedroom with queen bed. Quiet area, close to the down town 12-15 min drive and the restaurant in walkable distance. The playground is 1 minute walk. Would definitely stay there again and will recommend to friends.

Private Logan Square Garden Apt
Had a lovely stay at Janice's place! It is located a short drive from Logan Square, which has restaurants, bars, and a blue line metro stop. There was also a bus stop just outside the neighborhood. Speaking of the neighborhood, it was very serene and private, with plenty of parking regardless of the time of day. The airbnb is a basement unit, so maybe something to keep in mind if you're on the taller side, but it was spacious, and there was minimal noise from the floor above. Shower had great water pressure! Bedroom was clean and comfortable. Janice was very communicative and clear instructions were given for checkin and checkout processes.

Private Bed and Bathroom in a Great Location
It couldn't be better. No, it is not a luxury accommodation. It is the classic Airbnb, namely a room in a privately used apartment. Diana lives and works there alone. Above all, out of interest in foreign cultures, she rents a room with an opposite bathroom, which only the guests use. The accommodation is located in the Ukraine district, which is very quiet and about 30 minutes outside the downtown. In the morning, Diana surprised us with a prepared coffee machine (just turn it on), a few cookies and a lovingly prepared fruit plate. Bus no. 66 takes you quickly to the city center. We really enjoyed our time in Chicago. We received a lot of information from Diana, but also had very personal conversations. When we come back to Chicago, we'll check in with Diana! Thank you for the authentic and so lovely stay!!!
Family-friendly apartment rentals

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
Dean was the best host my girlfriend and I have had! He is proactive, friendly, great with communication, and provides everything you need for a great stay. Not only this, but the place was extremely comforting and beautiful! We had an amazing stay and would love to stay here again! Not to mention this place is an amazing price for how nice the stay was! Thank you Dean! You rock😎

Stylish 1BR with Laundry In-unit - Aberdeen G
Great spot for a stay in Chicago! Apartment is large, with a full living/kitchen, two bathrooms, and a bedroom with a big closet. It is walkable to the Fulton Market area and the blue line train. Aberdeen Tap is a great spot right down the street! Nick was quick to communicate and there were no issues with check-in. Place was clean and it was a great stay. Would book again!

Cool spot in cool neighborhood
Next to the trains, a apartment with separate bedroom, living room, kitchen and bathroom, even a laundry room available if necessary and a host who responds quickly and does not hesitate to give advice on Chicago. I highly recommend!

Bright & Spacious| Free Parking |Trendy Bridgeport
Local to the trains, we will consider it the next time we travel to Chicago.
Bright, Modern Apartment in a Vintage Greystone
From start to finish the communication and responsiveness from the owner was incredible. The property was immaculate and just super clean, and it was packed with everything you wouid need to be comfortable and feel right at home. We are definitely going to stay here again. Thanks for being such a great host Rob!

Kasa | Nearby Millennium Park | River North
Everything about this stay was perfect for a chicago getaway. Easy check in! Great price! Great view! All you need for 2 people - had everything equipped for cooking. Loved the breakfast restaurant and coffee shop downstairs. A dog park is only 1 block away - will definitely choose to stay here again! (Also great amenities!)
Explore the City from an Elegant, Urban Retreat
Our stay at Marissa’s went seamlessly! She was very responsive and accommodating ! Would stay here again :)

Level Studio | Fulton Market
This was the perfect place to stay in Chicago! Everything was nearby and the hosts were very friendly and responsive. The amenities provided were the best part; I enjoyed the rooftop, hot tub, and the views! I will be staying here again (:
Family-friendly apartment rentals

Lovely top floor 2BR/2BA, steps from everything!
The location was great. About 15 min from downtown. The place was beautiful and clean. I would definitely book with Julia again.

Modern Izakaya Studio in Wicker Park
My daughter and I stayed at Izakaya Studio on a recent visit to Chicago. The studio is great and Brett made it so easy to locate everything we needed to make our stay enjoyable. The next time we stay I hope to spend more time exploring the neighborhood because there were so many restaurants and shops to choose from (lots of open-air patios and decks which would be so nice during the summer season). The walk to the blue line El stop felt safe and quick. We loved the studio's layout. The kitchen and bedroom areas were separate and Brett has two big, comfy chairs for relaxing, and ample island space for eating or using as a work space. My daughter had some virtual work meetings and the Wi-Fi was reliable. The kitchen was well stocked with everything you'd need for meal prep. We ate out each day, but our delicious breakfast take-out came from a place right up the street called Yolk. I highly recommend the Izakaya Studio for a relaxing and fun visit to Chicago.

Your perfect place looks like?
In town for work and this was perfect place to stay for team. Easy walk to the shops and restaurants in Fulton Market while still providing a peacefully quiet setting. Bright, open and clean apartment with 3 large bedrooms. Nice kitchen for all meal-preparing needs If you don’t want to cook, no problem. Some of Chicago’s best restaurants are just a short walk or quick uber ride.

The Upscale Getaway Near Downtown
great location, the gated parking was exactly what i was looking for being there with a work truck full of tools. slept a lot better not parking on the streets of Chicago. beautiful condo with a nice view from the living room and back porch.

Newly updated 1BD/1B in Old Irving Chicago!
The time spent here was wonderful. This place has everything you need to feel at home away from home. Everything was clean and comfortable. The area was also really nice with tons of food and drinks within walking distance. The blue line is a short walk away and the busses run on the corner. I would definitely stay here again when coming back to Chicago.

Downtown Chicago - Spa Bath, Patio, 3 blocks to L
This is our 3rd time staying at Thomas and Cynthia place. We would have it no other way. Home away from home every single time.

Modern Hyde Park Getaway | UChicago
The apartment was clean and spatious, better than in the pictures. It's located in a corner of Hyde Park, at a 15 minute walking distance from the University of Chicago. It is a very residential area, with not many shops or restaurants near by, but if you walk 15 minutes east you will find bars, grocery stores and a few restaurants. I came to do research in the library's archive so it was very convenient. I had some problems with the door code sequence, but Erika was very helpful and responsive. My only suggestion is that more detailed information about the check in is provided, because not everbody is familiarized with lockers and codes! But my general impression was very positive! I'd definitely stay there again.

Spacious 4 Bedroom Condo
We had a great stay for an extended wedding weekend with our entire family. Adrian's home was clean, modern, and well appointed. The beds were all very comfortable and linens were very soft. We felt very safe and the garage parking spot was a nice addition. I would highly recommend his home and would not hesitate to rebook there in the future.
Quick stats about holiday rentals that are kid-friendly in West Loop, Chicago
Total rentals
90 properties
Nightly prices starting at
₹5,127 before taxes and fees
Total number of reviews
3.5K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
70 properties allow pets
Rentals with a pool
70 properties have a pool
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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
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Lincoln Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Illinois Beach State Park
- Willis Tower
- Wicker Park
- Washington Park Zoo
- Brookfield Zoo
- The 606
- Moraine Hills State Park
- Chicago Cultural Center