Vacation rentals in Near North Side, Chicago

5 out of 5 average rating, 11 reviews

Home in Lincoln Park

Top Floor in Historic Old Town!

MollyRating, 5 stars4 weeks ago

Wow such a beautiful space. The home was beautifully decorated with thoughtful artwork and really quality furniture. My first thought was “ omg, I want to live here!” Thank you Heather for sharing your space with me. You are so kind and made me feel right at home. I hope to be back. Be well, Molly

5 out of 5 average rating, 28 reviews

Home in Highland Park

Sanctuary on the Ravine

KathyRating, 5 stars8 months ago

The Woodland house is truly incredible, with every detail thoughtfully designed for comfort, from the cozy bedrooms and soft linens to the inviting beds. The kitchen nook with a couch overlooking the ravine offers stunning views of nature, making it a picturesque spot to relax. The home exudes warmth and is perfect for unwinding in the spacious sunken living room or one of the multiple outdoor seating areas. Debra was an excellent host, providing all the amenities you could need. This home is a 10+, and you won't want to leave!

4.91 out of 5 average rating, 123 reviews

Home in Homewood

Peaceful & Private Hot Tub Vacation Home Getaway

YoshiRating, 5 stars1 month ago

This small quaint home packs a HUGE punch when it comes to amenities and that home away from home feel. We couldn't have asked for more in an airbnb during our stay in the Chicago area. From the kuerig, to the decor, to the hot tub to the amazing bathroom and shower, this Airbnb had everything we needed and everything we didn't even know we wanted. I would HIGHLY recommend this airbnb along with the amazing and attentive hosts to anyone traveling through the area.

5 out of 5 average rating, 11 reviews

Home in Avondale

Alluring Avondale Abode

MichaelRating, 5 stars1 week 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.

4.85 out of 5 average rating, 68 reviews

Home in Austin

A Comfortable Stay While You are Away in Oak Park

KarenRating, 5 stars1 week ago

The house looked just like the beautiful photos & Jay was incredibly responsive throughout the visit. This home is located close to 290 to go downtown or further out to the 'burbs quickly. We needed a home to stay last minute, and Jay was accommodating to that as well - we were happy to find this spot with all the space we needed inside and out. As a bonus, we met neighbors who were very friendly.

4.85 out of 5 average rating, 34 reviews

Guesthouse in Evanston

Tiny house in West Village Arts District

JoelRating, 5 stars3 months ago

Lisa was a great host and this is a great place. It's a small house, but worked great for what we needed it for and was close to our family that live in Evanston. It was also a great price. Additionally, there were games which was nice because we had our child with us. I would definitely recommend this place and I will be staying here again when we're in Evanston, hopefully Lisa's schedule will be open!

4.95 out of 5 average rating, 104 reviews

Guesthouse in Oak Park

O'Malley Oasis!

AndreaRating, 5 stars3 months ago

Clean, beautiful space. Has everything needed and the most comfortable seating space to relax. Clear instructions, easy parking. Be aware that there are several stairs to enter as seen in the pictures. They are well maintained with a handrail. This was not an issue at all for us but could be for someone with mobility limitations. Otherwise one of the best places I have stayed in Oak Park. Hope it is available when I come back.

4.96 out of 5 average rating, 280 reviews

Apartment in Irving Park

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.

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What guests are saying

Family-Friendly 2BD/2BA Prime Location (+parking)

4.91 out of 5 average rating, 94 reviews3 weeks ago

We really enjoyed this location, especially the ability to walk to so many restaurants nearby. Old Town is a neat little corridor with many shops and places to eat, and felt very safe to walk to. Speaking of safety, being that we were staying in the city, I had no idea what to expect, but this place felt very safe, there is a locked gate to get on the property, then through another locked door before getting to the front door. Needless to say we felt very secure. Everything was very clean and tidy, and we had everything we needed for the few days we were there. Communication was also excellent and really prompt, while also being personable and down to earth! Although parking passes were provided, be aware that parking will likely be a challenge. We were only able to park using the zone pass once, and every other time we had to drive around for a while to find a spot, so be prepared to drop things off, park, and walk! Overall, great spot, great hosts! Definitely recommend.

Apartment in Old Town

What guests are saying

Premier 5BR/3BA Modern Retreat with King Suite!

4.91 out of 5 average rating, 23 reviews2 days ago

This home was GORGEOUS! Its was in a quiet neighborhood not too far from a shopping area. There is a play ground for small children near by. The 5 bedrooms were a great size. The king size bedroom included one of the bathrooms. The shower was AMAZING! The home was clean and smelled great. The bed felt like clouds. I feel asleep almost immediately every night.

Home in Elmhurst

What guests are saying

Great location-King beds-Kids playroom

5 out of 5 average rating, 50 reviews2 weeks ago

Ninna's place was fantastic! It was exactly as described, and the process was proactive. Ninna communicated very well and anticipated questions we may have. We had friends from the area join us for dinner, and Ninna was accommodating of that request. Her place was perfect, with everything we may need during our stay. The kitchen was stocked with all the things we needed, and the coffee nook was a nice touch! The kids enjoyed the little playroom upstairs, and the mattresses were very comfortable.

Home in Schaumburg

What guests are saying

The Hidden Beach House

4.75 out of 5 average rating, 8 reviews1 month ago

I enjoyed my stay here. The accommodations were basic, but the place was very clean and quiet, I found the bed very comfortable, and the location was ideal for 1 to 2 people to base out of while enjoying Old Town. The Brown Line train is just a couple of blocks from the house, which made getting to the Loop very convenient. Caid was very easy to reach with any questions. I would stay here again. One recommendation: if you drive here and need a parking pass, make those arrangements well in advance of your arrival, because they can’t be provided at a moment’s notice. I waited until the day before to ask for one and could not get it, so I had to pay $90 to park in a garage.

Guest suite in Lincoln Park

What guests are saying

Cozy 2 bedroom home in a wonderful neighborhood.

4.91 out of 5 average rating, 34 reviews4 months ago

I think this was my fav Airbnb yet. Convenient, very clean and a great kitchen! My dog enjoyed the backyard and the neighborhood was nice. I misplaced the house keys and Joanna responded immediately and had a solution! Thank you so much for that!!!! Would love to stay again when we visit family next year.

Home in Wood Dale

What guests are saying

Spacious 2 Bed Apartment, Perfect Location

4.89 out of 5 average rating, 73 reviews3 weeks ago

This is a quirky, comfortable place. It’s full of great books, interesting decor and Chicago charm. The apartment is quite large, it’s on the ground floor and there is back door access to the alley from the kitchen. The kitchen was full of cookware and there was a gas stove. I appreciated the coffee pot and large tin of Costco coffee. There was also a great selection of teas as well as many interesting mugs to choose from.

Apartment in Lake View

What guests are saying

Loyola & Lake -3br/2bth close to the Lake & Loyola

4.95 out of 5 average rating, 80 reviews3 months ago

My friends and I stayed for my birthday weekend and were super happy with everything, the fireplace is especially nice for cold chicago winters! We only had trouble finding street parking Saturday night when we got back from our concert at 3am but that was expected. This will be my go-to place for groups from now on!

Apartment in East Rogers Park

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Popular amenities for Near North Side, Chicago vacation rentals

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Stay near Near North Side, Chicago's top sights

United Center200 locals recommend

Millennium Park1,243 locals recommend

Navy Pier933 locals recommend

Lincoln Park Zoo1,117 locals recommend

Willis Tower Skydeck348 locals recommend

Au Cheval620 locals recommend

Other great vacation rentals in Near North Side, Chicago

4.92 out of 5 average rating, 38 reviews

Home in West Lawn

Family Friendly Duplex/9 min from MDW/Free Parking

AshleyRating, 5 stars1 month ago

Johanna made us feel warm and welcome. All amenities are included and work well. Excellent shower. She was very responsive and attentive.

5 out of 5 average rating, 5 reviews

Home in Chicago

Birthday?Anniversary?Showers?3500 sq ft, sleeps 16

ArissRating, 5 stars1 week ago

Vince’s place was amazing, it was such a good location, easy to drive to anywhere in Chicago. Vince was very easy to contact and was responsive within minutes. He made our stay very comfortable. The house was amazing and there was a lot of space, and there was a lot of amenities available for use, for example kitchen utensils and shower amenities. Overall this stay was amazing and I would book this again if I came back in the future

4.86 out of 5 average rating, 42 reviews

Apartment in Albany Park

Elegant 4Bedroom with Free Parking in Albany Park

MatthewRating, 5 stars2 months ago

Wonderful stay as always, thank you so much!

Apartment in Jefferson Park

4.63 out of 5 average rating, 24 reviews

City Gem: Stylish 3BR for Urban Explorers

AnnikaRating, 5 stars3 weeks ago

Peaceful, felt like home, very spacious and comfortable

Condo in East Rogers Park

4.79 out of 5 average rating, 29 reviews

Spacious condo with open floor plan and fireplace

TatianaRating, 5 stars3 months ago

This place was spacious and perfect for our family (two kids and a baby), with plenty of room for everyone to spread out. The hosts were fantastic! They encountered an issue with the fridge not working just before our arrival but handled it professionally, providing excellent support until it was fixed. We really appreciated their responsiveness and care. We highly recommend this space for families and large groups. One small suggestion: if you’re a light sleeper or have kids, consider bringing a noise machine, as some sound from the upstairs neighbors can be heard. However, this wasn’t a problem for us and is to be expected when staying in a condo.

5 out of 5 average rating, 25 reviews

Home in Lombard

Spacious Home in Chicago Suburbs

JenniferRating, 5 stars1 week ago

It was great! The house was lovely and looked newly renovated. It was much roomier than I expected. The beds were very comfortable.

5 out of 5 average rating, 4 reviews

Home in Wood Dale

Home in the Woods!

MaikoRating, 5 stars1 week ago

We had such a wonderful time at Jazmin Airbnb. The place was clean and smell great! She was very responsive and we had no issue with checking into our Airbnb. Thank you for being such a great host!