Vacation rentals in Riverside

4.99 out of 5 average rating, 353 reviews

Walk to Oak Park from Our Sunny Turn of the Century Apt

Soak up the vintage charm of this apartment dating back to 1908. This newly remodeled space is an elegant retreat, featuring 10-foot ceilings, local art treasures, and plush linens. A relaxing outdoor lounge area awaits after a busy day exploring. Pets are welcome on a case by case basis (contact host). The space is a charming two bedroom, one bathroom first-floor unit in a two unit historic home built in 1908. The apartment combines historic details with modern conveniences such as central heat and air, a dishwasher and washing machine and dryer access. The Monroe House is a stone’s throw from historic Oak Park and just three blocks from the CTA Blue Line making downtown Chicago a 25 minute train ride away. The condo includes additional amenities such as: •Smart TV for watching any account may you have (Netflix, Hulu etc...) •Central Air conditioning •Front and back porches for your enjoyment •Washer and dryer on site Just to the east lies historic Oak Park, and an array of attractions such as: •Brookfield Zoo •Chicago Architecture Foundation •Ernest Hemmingway Museum and Birthplace •Frank Lloyd Wright Home and Studio •Frank Llyod Wright’s Unity Temple •Oak Park Conservatory After taking in the local attractions, Chicago is only a train ride away, and it offers such noteworthy experiences as: •Shedd Aquarium •Architecture River Cruise •Skydeck Chicago •Navy Pier •The Field Museum •John Hancock Observatory •Adler Planetarium •Art Institute of Chicago •The Museum of Science and Industry You will have access to the entire unit and the basement so you can use the washing machine and dryer. We also have a back patio with a chiminea, patio table that seats 6, and a grill/smoker. You are welcome to use the backyard at anytime during your stay. We live in the top unit and are as available as you need. That being said, we very much respect your privacy and will not be checking in with you in person unless you request it. It is located in the Madison district, with acclaimed restaurants, pubs, and unique boutiques. Downtown Chicago is a 25-minute train ride away. The local brewery across the street offers delicious beers and creative meals for the whole family. We have a parking pad located behind our building. You can fit two cars on your side of the parking pad if they are parked in tandem. Some street parking is also available. We are located .4 miles from the CTA Blue Line train - Forest Park Stop. It is about a 6 - 10 minute walk from the flat. You can also take an Uber/Lyft into the city. It is about a 15 - 25 minute ride and it costs between $15 and $25. We are located about one mile from the Metra Station (Union Pacific West) and CTA Green Line - Oak Park Stop. Third bed is a queen sleeper sofa. We provide sheets and blankets for the sleeper sofa. You can smoke in the backyard. An ashtray is provided.

Superhost

Apartment in Berwyn

4.83 out of 5 average rating, 206 reviews

2bdrm, WiFi, WFH, W&D, parking, central location

Chicago has been voted Best Big City in the U.S. by for a historic 6 years in a row! Our space offers things like fast wifi, a comfortable workspace, and/or is suitable for children, our cleaning lady is immaculate. This is a Spacious, LARGE 2 bedroom 1 bathroom unit with assigned parking space, in the heart of Berwyn and in a safe multicultural neighborhood. Snacks, water, soft drinks and coffee. THIS APARTMENT has been professionally painted and has newer Close to Costco, markets and takeout.

4.97 out of 5 average rating, 142 reviews

1 bedroom garden apartment in Forest Park

Unique private garden apartment in our single family residence. Great location approximately 8 miles directly west of downtown Chicago. Close to shopping, dining, entertainment and public transportation to the city. One bedroom & best for 2 people but could sleep 3 ($50 fee) for short stays. It's important to note that this is a garden/ground/lower level apartment. The ceilings are relatively low at 6.5'. This would not be the best space for tall people. Free parking in front of the house.

4.86 out of 5 average rating, 117 reviews

City-Accessible Basement Retreat

Discover a perfect mix of small-town charm and city life in this cozy basement unit. Situated just a 7-minute walk from the train station, downtown Chicago is easily accessible for work/leisure. The neighborhood is a treasure trove of local restaurants, bars, and stores, ensuring you're never far from what you need. A convenient gas station/store is right behind your home for quick needs. Ideal for a simple, connected lifestyle with the city’s pulse at your doorstep. Your urban retreat awaits!

4.97 out of 5 average rating, 309 reviews

Apartment in Cicero

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy

Located on a tranquil city side street, this property is walking distance to numerous restaurants and stores. Enjoy easy access to public transportation, including Metra train, CTA Pink Line, and a direct CTA bus to Midway Airport. Downtown Chicago is a mere 20-minute drive away, with the United Center and Soldier Field just 15 minutes away. Ideal for a quick getaway, an overnight stay before your flight, or an extended work assignment. Unwind on the patio, complete with a fire pit and grill.

4.99 out of 5 average rating, 146 reviews

Home in Berwyn

Retro Modern Bungalow | fire pit | free parking

Experience the city in style at Retro Modern Bungalow—the perfect pad for up to 4 friends. Featuring two spacious bedrooms, each with a king bed and luxury linens, a propane fire pit and a fully fenced [pup-friendly] back yard. Enjoy central HVAC, hi-speed WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

Guest suite in Brookfield

5 out of 5 average rating, 101 reviews

Charming Chicago suburb! 1 bedroom apartment.

Enjoy your stay just west of Chicago in our 1880 updated 1st floor of a 2 flat. You get a one bedroom apartment with queen bed, private kitchen and bath, separate office for work, plus 2 porches for you to enjoy. Brookfield is a charming village with unique restaurants, bars, salon and day spa, coffee shops, library and the train to Chicago--all within a 5 minute walk. We want you to feel at home; but before you book understand that you may not smoke ANYTHING in the unit or on the property.

Superhost

Apartment in Oak Park

4.82 out of 5 average rating, 122 reviews

Circle Back Modern Apartment

Sit on your leafy private patio and enjoy your coffee before heading out to the city- or wind down at the end of the day with a cold beer. Steps to coffee shops, neighborhood pubs, and the Blue Line train this beautifully updated and decorated apartment is the perfect landing pad for your Chicago adventure. FREE off-street parking, free in-unit laundry, a cute coffee station- basically every amenity we could think of! This will be the place you want to stay every time you visit Chicago.

4.82 out of 5 average rating, 280 reviews

Home in Forest Park downstairs.

Enjoy a private ground floor apartment which is centrally-located with easy access , to the city. You will have a functional kitchen, laundry facility outside your back door and fast internet. Forest Park is located about 20 minutes from downtown Chicago and about 30 minutes from O’Hara international airport. You are within walking distance of many boutiques, restaurants, parks and also public transportation. Please make a note that there will be a $30 per guest fee if more than four.

Superhost

Apartment in Berwyn

4.82 out of 5 average rating, 51 reviews

10 min from Midway/ Downtown Chicago apartment

Welcome to our Cottage Home! Enjoy a super cozy, clean, and private first-floor 2-bedroom, 1-bath space in a charming three-story home. Please note: this listing is for the first floor only. The upper levels are occupied separately, but you’ll have full privacy on your floor with a private entrance. We are located in the vibrant suburb of Berwyn, just 15–20 minutes from Downtown Chicago. You’ll find plenty to explore nearby — amazing restaurants, parks, shopping, and attractions.

4.95 out of 5 average rating, 324 reviews

Mid-Century Charm. Near Chicago. Low Cleaning Fee!

Step back in time a bit with our charming 2nd floor walk-up in a quiet, safe suburb. Parking included on-site. Vintage, welcoming vibe. We're a 20-30 minute drive to downtown Chicago (depending on traffic). The unit is on the 2nd Floor and is separate from the rest of the house (we live on the 1st floor). 1 Dedicated Guest Parking spot (included). Additional Free Parking is available. Great wifi. 3-season back porch. Record Player (Real Vinyl!)

5 out of 5 average rating, 306 reviews

Like a Treehouse!

If you're coming to Illinois for any medical procedure that's no longer available in your home state, reach out to us about discounts. You'll feel like you're in a tree house in our 850 sq ft coach house, above our workshop/garage, behind our home in historic Forest Park, right next to Oak Park. Just 8 miles west of Downtown Chicago, convenient to I-290 and the Blue Line train.

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Other great vacation rentals in Riverside

Private room in Willow Springs

4.93 out of 5 average rating, 278 reviews

Private bedroom A in a quiet Chicago suburb.

RodrigoRating, 5 stars6 days ago

Had a nice time, was flexible about parking spots.

4.94 out of 5 average rating, 304 reviews

Private room in Oak Park

Single bedroom with Asian decor in family home

JiantingRating, 5 stars4 days ago

Very friendly and accommodating hosts. Felt very welcome.

4.97 out of 5 average rating, 123 reviews

Private room in Berwyn

Private lower level suite suburb Chicago

JasmineRating, 5 stars5 days ago

Aurora was an amazing host. We had just stayed one night because we were just in town for a WNBA game. the arena was close to the house, which was nice. I loved how close she lived to the city but also far enough that the neighborhood was quiet. In the morning when we woke up Aurora had gave us nice suggestions for breakfast and it was a really good restaurant. Aurora was also super helpful when I needed help with the TV because it wouldn’t turn on and she came right down to fix it! She also had water and snacks laid out for us, which was also very nice and comforting.

4.99 out of 5 average rating, 217 reviews

Private room in Elmhurst

Chic Oasis near Downtown Chicago

Bella Rating, 5 stars5 days ago

Thank you Jan for welcoming me into your home. Jan communicated very well throughout the stay. She went above and beyond to make sure we enjoyed our stay. Bless you!

Apartment in North Riverside

4.75 out of 5 average rating, 36 reviews

Spacious, Renovated Suburban 2-Bed Near Chicago

RavitejaRating, 5 stars2 months ago

Place was excellent and its worthy for what we paid for but couple of power outlets are not working other than that everything is good and I liked it

Private room in North Riverside

4.93 out of 5 average rating, 214 reviews

The Albany Park Room at the Cape Cod in Riverside

MingleRating, 5 stars5 days ago

The place was a wonderful stay — both the bathroom and bedroom were exceptionally clean and well-maintained. However, if you’re planning to travel by car, I recommend reviewing the house rules carefully before booking. First, the driveway only accommodates one-way traffic for a single vehicle at a time. Second, street parking is prohibited between 2 AM and 6 AM. These two rules combined mean that guests must park in the driveway overnight. However, the host typically needs access to the driveway early in the morning. The host offers to move guests’ cars to the street in the morning. While this is a considerate idea, especially for those who don’t want to wake up early just to move their car, we felt a bit uneasy about it. Having previously experienced a street parking accident, we wanted to avoid any added mental stress associated with someone else moving the car for us. And it will be hard to argue with the insurance if the host was hit when trying to move our car.