Kid-friendly holiday rentals in Bridgeport, Chicago

Erik was a phenomenal host, went above and beyond to ensure we had a comfortable stay at his house. His family were lovely people and helpful with any and all questions. Erik gave is good clear instructions on the best places to go to in the area, how to travel to the city and how to use all the appliances/facilities in the house. I couldn’t recommend him any more, he made our stay really more comforting and laid a great basis for our stay in Chicago. Cheers Erik!

Abby was more than a wonderful host! She's very thoughtful, friendly, and responsive. Whenever we needed something, she was happy to accommodate us. We always enjoyed the conversations with Abby when we ran into her in the living room or kitchen. Abby is also very kind - we were curious why so many street cats were gathering near her house and backyard and it turned out that Abby has been feeding them with dry and canned foods. Needless to say, Abby's house was very lovely and clean, and the location was wonderful, but more importantly, Abby was a wonderful host!

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

Amazing stay. 15 minute walk to the L and a short ride to downtown, my fiancée and I walked to the target down the road for a few breakfast items. Quiet neighborhood too. Bathroom was amazing. The place is pretty high tech. Recommend this Airbnb highly.

This exquisite MCM GEM in Berwyn was the perfect home base for us while visiting Chicago. Every corner is curated with unique and authentic MCM touches, all with the contemporary creature comforts one could want and then some. Everything was sparkling clean and April was a superb host. We hope to come again, & highly recommend!!

One of the best Airbnbs I have stayed at. It was beautifully decorated and super clean. Had everything I needed to feel comfortable and at home. The host was extremely responsive. The parking was a bit difficult but would not deter me from staying there again. Very close to downtown, about 10 minutes. Highly recommend.

I loved my stay, close to the CTA , you can get from the airport to the house only using public transportation. A train ride from the city The room matched the description, so make sure to read it ! I stayed there for the house vibes and it was great for me. Thank Ryan, I’ll probably stay again.

Enjoyed my stay, very clean and comfortable. Very convenient and close to airport, train station, bus stop, etc. The host is amazing and responsive to guest’s needs.

I had a wonderful stay at this cozy garden apartment! The space was exactly as described—clean, comfortable, and thoughtfully set up with everything I needed. I especially appreciated how quiet and peaceful the neighborhood was, yet still close to everything. The location made it easy to get around, but it also felt like a relaxing retreat after a busy day. The setting added a nice touch of charm and tranquility. I’d definitely stay here again—highly recommended!

Great place in a good location! Wonderful neighborhood. Was easy to find and near main road on a frontage road, but you would never know it by how quiet things are. Highly recommended.

Cam’s place was a great find — spacious, clean, and surprisingly quiet despite being on a busy street. The photos don’t do justice to how much room there is. The layout is unconventional but adds character, and everything is well thought out. The kitchen is fully stocked, there are plenty of towels, and the TV area is perfect for relaxing, comes with private parking. Located in a safe neighborhood just minutes from the Orange Line, it’s super convenient for getting around Chicago. I already miss this place — absolutely worth every penny.

This place was amazing!! Felt right at home as soon as we got there. The neighborhood is very quiet and chill, there’s a ton of great mexican food/stores, and just a couple blocks from the pink line and bus stop. Great home base just outside of the chaos of downtown but easy to get anywhere you wanna go! The place itself was comfortable and felt very roomy. Only thing is there are some upstairs neighbors who you WILL hear walk, talk, breathe… but we didn’t have trouble dealing with it and still slept well. Plus they had two cute little doggies who came to say hi, which is a huge plus! Overall 10/10 would stay again and would always recommend to anyone visiting Chicago.

5 star for sure! This place is a hidden gem, its so clean and has so many little extras to make you feel at home. I found seasoning to cook with,.coffee, tea, cream and sugar..and even a couple of pods for laundry. All of that plus an easy check-in, great parking space in the back (which you will need since street parking can be dicey) and the friendly neighbors made my stay wonderful. I stayed 7 nights and it is quiet at night so I felt very safe and got a good nights rest each night. I will definitely book again!!!

This is a gem in the heart of the Bronzeville neighborhood, very underrated in comparison to most other neighborhoods in the City. The place was charming and functional (perfect for sleeping, watching movies, and eating a quick meal. I've definitely got some pleasant moments here - there's a park across the street that helps with the calmness. This is a good spot to check out a view of Chicago that few appreciate - I (being a former resident) really appreciate the opportunity and spot that Rosemary ,has offered and would love to come back!

Loved our stay at The Foundry! The unit was beautiful and comfortable and the views were incredible. We had everything we needed and communication from Cloud9 was clear. There are great places nearby to walk for coffee and food — including an amazing Whole Foods.

Well kept, quiet environment. Host is responsive.

When we were first looking for a place to stay, none of the available AirB&Bs looked great. A week later, we looked again, and suddenly Julia's place popped up. It was so much better looking, and with a fairer price, than any others I could find in the list. A two-bedroom that is a *real* two-bedroom, for the price that others were charging for a pull-out bed in the living room. It was just as beautiful in-person. We felt immediately at-home and comfortable. I'm someone who has insomnia, especially while traveling, but there, I had no problem sleeping somehow. Also, it truly is a short walk to the Blue Line, or even a just few steps from the 77 bus route, which goes to the Blue Line, or all the way right into downtown Chicago.

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.

I stayed at John’s Airbnb during my trip to Chicago, and I honestly couldn’t have asked for a better spot—especially being right in the heart of Chinatown. The place was spotless, super cozy, and had everything I needed for a comfortable stay. You can tell John takes pride in keeping it clean and well-stocked, which I really appreciated. What made it even better was the location. Chinatown in Chicago is such a vibe—full of culture, energy, and some of the best (and most affordable) eats in the city. If you’re a foodie like me, you’ll love exploring all the spots nearby. One place I highly recommend is Hing Kee. Their hand-pulled noodles and dumplings are on point—fresh, flavorful, and easy on the wallet. If you’re looking for a clean, convenient, and authentic Chicago experience, especially in Chinatown, John’s place is the move. I’d definitely stay here again.

Good location. Condo was very clean with comfy beds. There are 3 flights of stairs to get to condo- no problem for us but be aware

Great stay at Anne’s place. She was very communicative and went out of her way to ensure we were comfortable. We would definitely recommend to anyone coming to the Chicago area!

Walid was very kind, and the place is exactly as described. The beds are incredibly comfortable, and overall, the space is very pleasant. I definitely recommend it!

Crazy clean, super breezy place to stay. Neighborhood is fine, but not a lot of amenities. But it was a great place for us to be.

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.