Vacation rentals in Chicago Loop

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Chicago Loop

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Guest suite in West Town

4.96 out of 5 average rating, 338 reviews

Secret Garden @ The Noble Farmhouse | Wicker Park

While our place truly is a tucked away secret sanctuary, we are also in a sweet spot of ULTRA CONVENIENCE. Wicker Park/Noble Square/West Town has many great bars & restaurants & is an amazing location for exploring the city. WALK to the action on Division St. or Chicago Ave, Chicago's upcoming gallery district. A 1/2 block to the 56 bus takes you to the Loop in 10 min, or to the heart of Wicker Park in 5. A 10 min walk to the BLUE LINE serving O'Hare & Downtown. And Divvy bikes 1/2 block away.

Guest favorite

Home in Lincoln Park

5 out of 5 average rating, 11 reviews

Top Floor in Historic Old Town!

Unbeatable Location in Historic Old Town Triangle! This charming top-floor apartment is on a quiet cul-de-sac in the heart of Old Town Triangle, steps from St. Michael’s Church, North Ave Beach, Lincoln Park Zoo, and Wells Street’s entertainment district. The sun-filled space features an oversized private patio, and 3 bedrooms with queen beds, closets, and dressers. The spacious kitchen and dining areas are perfect for gatherings. The “L” stop is just two blocks away for easy access to the city.

Guest favorite

Apartment in West Lake View

4.94 out of 5 average rating, 175 reviews

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

Welcome to beautiful Roscoe Village! Come relax and enjoy a gorgeous loft-like condo that has a huge sun-drenched living room and opens up right to the kitchen. Enjoy cooking on your own in the spacious kitchen and rest easily at night in a spacious king bed in the main bedroom. We love and welcome pets - so no need to leave your fur baby at home. Uber to Wicker Park and Logan Square. You’ll have your own private entrance with a lock box to get into the condo. We look forward to hosting you!

Guest favorite

Home in Lake View

4.88 out of 5 average rating, 169 reviews

Lake View | Wrigley Designer House w/Patio

Between Wrigley Ville and Lincoln Park, our home is on a quiet street. We are surrounded by coffee shops, restaurants and nightlife. There is a Whole Foods less than a block away, a Target and other groceries stores within 5 minutes walk. The house is over 2,500 square feet spread over 3 floors, with 4 completely separate bedrooms. Extra tall ceilings in the common areas, artsy cathedral ceilings and skylights in the upstairs bedrooms and very comfortable mattresses will help you unwind.

Top guest favorite

Home in Avondale

5 out of 5 average rating, 11 reviews

Alluring Avondale Abode

Welcome to Alluring Avondale Abode, the perfect vacation rental for your next family trip or group getaway. A pet-friendly paradise, centrally located for easy travel to all the top attractions. A spacious kitchen, beautiful backyard deck, and patio create a wonderful backdrop for entertaining and relaxing. Find an array of fun games to keep all ages occupied. Book now and experience the laid-back vibe and unbeatable amenities that will make your vacation truly unforgettable.

Superhost

Home in Austin

4.85 out of 5 average rating, 68 reviews

A Comfortable Stay While You are Away in Oak Park

Welcome to this Oak Park home, conveniently minutes from the main expressway, train station, downtown Chicago, and the Medical Center. This entire Oak Park house is ideal for travelers seeking a tranquil and welcoming space to unwind in after a long day, medical professionals, visiting patients at the Medical Center, and families needing long-term housing. The residence is minutes from downtown Oak Park and the historical landmarks of Frank Lloyd Wright's home and studio.

Superhost

Apartment in Logan Square

4.92 out of 5 average rating, 12 reviews

2-level PH w/ 2 Luxe Suites Combined; Spa Access

The top floor sprawling ranch with duplex down offers sky & outdoors views, privacy, & cathedral ceilings, it is connected to your rear 2nd floor suite with 10ft ceilings. A burgeoning neighborhood next to the 606 Trail Amenities: - Uber-fast Wifi streaming, - Hot tub house - 80" + 75" hi-def tv's - 3 sectional couches - European decor - 2 kitchens - The popular 606 Trail access is 100 ft away, - YMCA across the street with indoor Olympic size & kiddie-pools!

Guest favorite

Apartment in Lake View

4.94 out of 5 average rating, 115 reviews

The Wrigley Flats | Chicago Vacation Rental

The Wrigley Flats is a unique Chicago vacation rental located 4 blocks south of Wrigley Field in city’s most sought after north side neighborhood---Wrigleyville! Our 3 bedroom | 1 bathroom flat can be rented for a weekend getaway, a week long vacation or an extended stay. Close proximity to Chicago’s lakefront, vibrant nightlife, the eclectic dining scene & of course Wrigley Field; it’s no wonder visitors flock here to get a taste of something amazing!

Guest favorite

Guesthouse in Evanston

4.85 out of 5 average rating, 34 reviews

Tiny house in West Village Arts District

This tiny house (750 sq ft) invites you to explore Evanston's West Village Arts District and shop creative businesses. Just down the block is the newly renovated Robert Crown Recreation Center, where you can check out library books and movies, play soccer, tennis, ice hockey and go ice skating year round. This Tiny House is located in our backyard, so please be respectful of noise and the amount of guests you book on the reservation!

Superhost

Apartment in Lake View

4.89 out of 5 average rating, 73 reviews

Spacious 2 Bed Apartment, Perfect Location

Located just blocks away from the Brown Line CTA stop, This massive 2 bedroom apartment will add some vintage charm to your vacation in a safe, low key neighborhood while never taking you far from the action. This unit is ideal for travelers looking for a comfortable home base while exploring everything downtown and the north side of Chicago have to offer.

Guest favorite

Guesthouse in Oak Park

4.95 out of 5 average rating, 104 reviews

O'Malley Oasis!

Your home away from home at this centrally-located coachhouse apartment.Queen sized bed, fully equipped eat-in kitchen, relaxing living area with recliner, leather couch and big screen tv. Walk to downtown or explore Chicago via public transportation just a few blocks away. Adorable porch and your own entry. Parking spot included!

Top guest favorite

Apartment in Irving Park

4.96 out of 5 average rating, 280 reviews

Spacious 1BR apartment in a central location

Private 1BR in Avondale neighborhood of Chicago. Right off the Expressway, it's 20 mins from O'Hare, 20 mins from Downtown (both by Blue Line) 20 mins from Wrigley Field (bus). Comfortable and spacious attic apartment in a residential area. Lots of street parking.

0 of 0 items showing

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 reviews3 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

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

Private Downtown Retreat with Rooftop Oasis

4.98 out of 5 average rating, 43 reviewstoday

Florin was an amazing host! Seemless check in and wonderful location. I still can't believe how clean this place was. I'm very picky about cleanliness and I felt so comfortable no matter what room I was in. This was our first trip to Chicago and everything we needed was in walkable distance. The location was spot on and it was a very beautiful part of the city. This will definitely be our go to place to stay next time we are in the area.

Home in Near North Side

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

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