Vacation rentals in Berwyn

2 bedroom• 3 beds • 1 bath Apartment in Berwyn

Enjoy a stylish and elegant experience at this centrally-located private apartment On famous Route 66. Sunny, clutter free very spacious 2nd floor. Apt. Can sleep upto 6 ppl. Inflatable bed added for extra sleep option. Prepped for photo sessions of your own. •Restaurants, Auto repair shops and Walgreens are walking distance and much more. •Metra is a 10-15 minute walk. •DT Chicago 18 min •Brookfield Zoo 15 min Away •Midway Airport 15 min •O’Hare Airport 30 min •Mall 10 min •Loyola Hospital

Cozy & Peaceful Oasis Near City | 2BR + 1.5 Bath |

Unwind in this stylish 2-bedroom home in Berwyn just 20 mins from Downtown Chicago and Midway Airport. Berwyn is full of award-winning restaurants, bars, shops, & attractions. Adventure through Chicago from this prime location with ample street parking, accessible highways, and public transportation. Enjoy the private backyard during the summer months, relax on the hammock, and even grill a delicious meal! • Full Kitchen • 2 Bedrooms • Private Backyard • High-Speed Wi-Fi • Pool Table • 2 Levels

1 bedroom garden apartment in Forest Park

Unique private garden apartment in our single family residence. 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 we have pets (cats/dog) in this home and also 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.

Contemporary NEW Entire Suite Berwyn/Riverside

Welcome to your private oasis! This beautifully NEW appointed 1 bd unit offers the perfect blend of modern convenience and contemporary style. Whether you’re here for a weekend getaway or an extended stay, this contemporary retreat is your perfect home base. Explore the vibrant attractions of Berwyn or the excitement of Chicago, just a short trip away. Book today to secure your stay and experience the blend of comfort and style in this chic contemporary gem. We look forward to hosting you!

Private apartment with retro vibe

Cozy 1 BR apartment with retro touches in Berwyn a block from Oak Park. 2nd floor private apartment. Wifi, cable, premium channels. Full kitchen. Queen bed plus brand new twin sofa bed, + 1 more twin 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, great bakery. NO smoking, candles or glitter! (Yes, I truly needed to add the “no glitter” rule! (You can only imagine!)

RetroModern Bungalow | free parking | pet friendly

Experience the city in style at our Retro Modern Bungalow, the perfect pad for up to four friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a pup-friendly, fenced-in backyard. With central HVAC, speedy WiFi, a dedicated workspace, and a pack-n-play crib 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 and catch the train a few blocks away.

The Architectural Haven

Welcome to The Architectural Haven! Enjoy comfort and luxury in our modern Berwyn bungalow, a serene escape only 15 minutes from downtown Chicago. Nestled in a charming neighborhood, this secluded retreat offers the perfect place to relax and recharge. Our thoughtfully designed space is fully equipped with premium amenities and unique architectural touches. Every room invites you to feel at home, ensuring a memorable stay you’ll want to revisit We look forward to hosting you!

Beautiful Bungalow, Near Downtown Chicago

Beautiful, cozy, vintage home in a centrally located quiet neighborhood. Close to downtown Chicago, O'Hare and Midway Airports as well as many attractions, museums and great places to eat. This home includes High Speed Wifi, Full Kitchen, Full washer/dryer, tv's with streaming and a game loft full of board games and game consoles for all guests to enjoy. Contactless check-in and check-out with keyless entry. 3 Bedrooms, 4 queen beds, 1.5 baths. Sleeps 8 guests total.

House to Relax

The whole group will enjoy easy access to everything from this centrally located place. Public transport is in front of the house, so you will get easy access to any place. Downtown Chicago is very close and shopping center is few blocks away. This place is quite big, super clean and you will have a lot space for all the family. In this place you'll find all the dishes to cook if you want. It's very close to supermarkets, restaurants and a lot different stores.

Bright Boho Haven free parking

Welcome to our bright, newly constructed 1-bedroom, 1-bath Airbnb in the heart of Oak Park. Enjoy a sunny, modern space with a beautiful bathroom, free parking, and all the essentials. Just steps from grocery stores, coffee shops, and the Oak Park Blue Line stop—reach downtown Chicago in under 30 minutes. Perfect for a cozy getaway or work trip, with fast Wi-Fi, smart TV, kitchenette (no oven!) and a peaceful, walkable neighborhood. We can’t wait to host you!

Bright & Spacious Victorian-FREE PKG walk to train

This historic Queen Anne home built in 1889 is in the heart of Oak Park. Walk to all tourist attractions, public transportation that takes you directly to downtown Chicago, 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.

Coachhouse in central OP 4 blk to L

Just updated, furnished 1 BR 1 BA apt in Frank Lloyd Wright Historic District. Parking, kitchen, washer/dryer in unit, Air/Heat, Smart TV. Free wifi. Central location: 1 blk to farmers market, near Hemingway / Frank Lloyd Wright attractions. 4 blocks to green line. 20 min ride to downtown Chicago. Available for longer term stays.