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!

Great place to stay. Good area. Walking distance to a lot of stuff

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.

Samantha was a wonderful host—she was very responsive and proactive in resolving any difficulties I faced, always with kindness. The space itself was spacious and well-suited for a family stay. I especially appreciated how well the bed was maintained, with a comfortable mattress and clean bedclothes. I would definitely choose this place again next time I travel to Chicago. My sincere thanks to the host!

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.

Great

My family and I enjoyed staying here. I was born and raised in Chicago just 4 blocks from this Airbnb! It was such a great experience to be back in my old neighborhood. Olusesan is a phenomenal host! I highly recommend this place.

This was my first Air Bnb stay & it was 1000% worth it. I stayed at the Marriott OHare for two nights then came here for another two nights and I felt more comfortable, slept better and more at home here. I was able to walk peacefully back after a day in the city with no issues. I was a bit skeptical about the shared space but it was if no one else was really there and the one person I saw was so pleasant and respectful. I would definitely be back here! It felt like my home away from home.

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!

I can’t say enough good things about how responsive and helpful Milan was. My first morning the coffee maker wasn’t working, so I messaged him and within a few hours he had delivered a replacement coffee maker. As it turned out, the original coffee maker worked fine the rest of my visit so I didn’t need the new one, but I was impressed with his fast help. I would certainly be happy to stay here again. It’s a great location and quite comfortable.

This listing is exactly like the pictures, no frills but comfortable and at a great price. We had family living close by so the location was perfect, will stay again. Thank you!

Looked just like the photos/description. Convenient location - in front of a bus stop and near a train station. Easy check-in. Initially had some trouble getting hot water from the shower but Cam was responsive and was able to address quickly.

Khong was responsive, helpful, friendly and overall just a cool host! Khong gave us a sweet surprise when we got in and gave us local recommendations, we loved the Back of The Yards Coffeehouse and it was within walking distance. During the day it felt like a safe neighborhood, during the night it was very lively and full of people in the best way. Khong’s place was so clean and inviting. The backyard was peaceful with a beautiful view of the church. We did have a slight mishap occur when we lost the keys to Khongs place but he was very understanding and kind about the situation. Our stay was everything we hoped for and more. We would definitely return the next time we are in Chicago! 10/10 recommendation from my family and I

Really enjoyed the spaciousness Carmen’s place offered my brother and I. The living room was my fave with its open concept. Just be vigilant at night and you’ll be fine. Don’t hesitate to book!

We truly had the best time staying at Alec’s. The space is lovely, comfortable, and has everything you’d need. The outdoor spaces were beautiful and private with a high fence surrounding it. We enjoyed spending time by the fire and the neighborhood is great. Our favorite part by far were Alec’s two lovely pups Molcajete and Lobita. They were absolute ANGELS and made us so happy- we hated leaving them. Alec was a great host- super communicative, friendly, and just what we needed. When we come back to Chicago, we’ll definitely stay with him again.

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!!!

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.

747 Lofts is super conveniently located, right near a stop for the blue line. Lots of great food nearby, we loved getting coffee and scones at Big Shoulder every morning. Host was very responsive, always friendly and helpful. Great communication, great location, would 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!

Everything went well. Place was very nice and the host was very responsive when I needed help and accommodative as well. Highly recommend if needed a place near downtown.

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.

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.