Holiday houses in Cicero

4.92 out of 5 average rating, 381 reviews

Private apartment with retro vibe

Gunderson Getaway is a cosy one BR apartment with some retro style touches in Berwyn a block from Oak Park. 2nd floor private apartment. Wifi, cable, premium channels. Full kitchen. Queen bed plus sofa & extra single bed available. EASY free street parking right by unit. Quick drive to City. Convenient to both airports, United Center and walk to Fitzgerald’s Club. Near Blue Line, restaurants, groceries, great bakery. NO smoking, candles or glitter! Pets MUST be pre-approved and never left alone.

4.86 out of 5 average rating, 118 reviews

Apartment in Forest Park

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, 310 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.

4.9 out of 5 average rating, 302 reviews

The Green Bungalow: Charming 1-BR apt. with patio

Situated in a residential neighborhood just outside the city limits, this lovely 2nd floor apartment is blocks from the Blue Line train and highway. Our newly renovated vintage unit has a full kitchen, hardwood floors, plenty of natural light, a backyard patio and its own private entrance. Our bungalow is walking distance to cafes, restaurants, shopping, music and nightlife. Enjoy the charm of the suburbs while having easy access to all the attractions Chicago's downtown has to offer.

Superhost

NEW Jade Haven in Berwyn/Riverside

Step into Jade Haven, where tranquility meets modern elegance. This serene one-bedroom, one-bath suite offers a peaceful retreat, inspired by the calming essence of jade. The space features a sleek, airy design with thoughtful touches to make you feel right at home. Fully equipped kitchen, cozy living area, the bedroom invites restful nights, while the spa-like bathroom offers a moment of quiet indulgence. Perfect for a restful getaway or a productive stay.

4.97 out of 5 average rating, 199 reviews

Apartment in Oak Park

Modern+Spacious W/King Bed, Walk to Town-Park Free

This historic Queen Anne home built in 1889 is in the heart of Oak Park. Centrally located and within walking distance to all tourist attractions, public transportation, great restaurants, boutiques and grocery stores. It’s the perfect base for exploring Oak Park and Chicago We kindly ask that you read our full listing description and our house rules prior to booking. 4 guests maximum-no visitors allowed

Superhost

Apartment in Cicero

4.87 out of 5 average rating, 105 reviews

Modern Cicero apartment

The drive is 11minutes from Midway. It is in Cicero, IL. The neighborhood is peaceful with friendly neighbors. 6 guest max in the property. We have street parking available. It has great appliances and the tub comes with a jacuzzi. There is a backyard as well that is shared with the neighbors but can be utilized. We plan to make your stay as comfortable as possible to enjoy your experience in town.

4.94 out of 5 average rating, 241 reviews

Condo in Oak Park

Picture Perfect 3Bed Steps from Train and FLW

Welcome to your beautiful 3 bedroom home-away-from-home! From the Instagram-worthy forest room to the cozy fireplace reading nook to the modern ice crusher in the kitchen, we've put so much thought into this home that we're sure you won't ever want to leave. Welcoming and newly updated, this unit is close to restaurants, shopping, the best of Frank Lloyd Wright, and the train to the city.

4.95 out of 5 average rating, 227 reviews

Spacious Oasis Berwyn with Free Parking

Welcome to Spacious Oasis Berwyn! Make your stay in the area easy. Take advantage of our centralized location where most destinations are only 20 minutes away by car and public transit is less than a block away. Great food, parks, nightlife, and shopping are all within walking distance. Whatever brings you to "My Kind of Town", our oasis is sure to please with ease.

4.9 out of 5 average rating, 126 reviews

Condo in Berwyn

Picturesque Apartment in Berwyn

This stylish place to stay is perfect for group trips. 2 bedrooms with queen beds, spacious living room with a sofa bed and well equipped kitchen. The apartment is located in North Berwyn, 15 minutes drive from Downtown Chicago, walking distance to Roosevelt Road's bars and restaurants, 0.8 miles to CTA Blue Line rail line station.

4.98 out of 5 average rating, 191 reviews

Bungalow in Berwyn

3BR Home w/ Free Driveway Parking | Near Chicago

Discover the allure of our nestled haven in the suburb of Berwyn, just a 20-minute drive from downtown Chicago. Recently remodeled, this stylish retreat offers comfort in a tranquil neighborhood—an ideal escape for both business travelers seeking respite and families on vacation.

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4.94 out of 5 average rating, 304 reviews

Private room in Oak Park

Single bedroom with Asian decor in family home

JiantingRating, 5 stars6 days ago

Very friendly and accommodating hosts. Felt very welcome.

4.78 out of 5 average rating, 73 reviews

Cozy & Private 1 BR Near City + Airports

DanielRating, 5 stars2 weeks ago

Super clean place really enjoyed my stay.bathroom a little small but overall everything was as expected as he described really nice would definitely stay again.

4.97 out of 5 average rating, 123 reviews

Private lower level suite suburb Chicago

JasmineRating, 5 stars1 week 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.

Superhost

4.87 out of 5 average rating, 55 reviews

The Quilt Room. Micro-flower farm.

TaliahRating, 5 stars1 week ago

The home was perfect for our trip to chicago! We will definitely come back again

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 stars1 week 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.

5 out of 5 average rating, 9 reviews

Private room in Oak Park

DT Oak Park LUXE Private BR C | Queen Bed Sleeps 2

YanitRating, 5 stars2 weeks ago

I had a great stay at this place! The location was absolutely perfect—close to grocery stores and everything I needed was easily accessible. The bedroom was definitely my favorite part: super comfy bed and a spacious closet that fit all my luggage with ease. Everything was clean and well-maintained, which made the stay even more enjoyable. Parking is on the street and not included, but there was plenty of space and could park right in front whenever I needed which was a huge plus. Would definitely stay here again!

4.93 out of 5 average rating, 61 reviews

Nice cozy room

AnaRating, 5 stars1 week ago

Our stay at Dolores's house was very good. The location was excellent, with easy access to public transportation and the market. The room was clean and organized. The common areas shared with other guests were a bit messy, but that was probably due to the behavior of the other guests and not the host’s fault