Condo vacation rentals in Oak Park

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Top-rated condo rentals in Oak Park

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Guest favourite

Condo in Avondale

4.96 out of 5 average rating, 118 reviews

Lovely top floor 2BR/2BA, steps from everything!

BEST LOCATION IN LOGAN SQUARE/AVONDALE!! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops. Free parking on Lawndale Ave.

Guest favourite

Condo in Mayfair

4.88 out of 5 average rating, 128 reviews

Newly updated 1BD/1B in Old Irving Chicago!

Welcome to your home away from home in the heart of one of Chicago's safest and quietest neighborhoods! This beautifully updated 1 bedroom apartment offers everything you need for a comfortable and convenient stay. It is perfect for couples, solo travelers, and business visitors. Book now for a truly unforgettable experience in the Windy City! - 1 free parking spot - 400 MB Wifi - 2 smart T.V. with access to Netflix, Hulu, Amazon and more! - Desk - Easy app paid laundry in the building.

Guest favourite

Condo in Berwyn

4.93 out of 5 average rating, 108 reviews

3 Bed Vintage Condo In Chicagolands Trendy Berwyn

Start your adventures in this lovely three-bedroom hidden gem in Berwyn, just minutes away from Chicago and everything the city has to offer. Enjoy an abundance of natural light and comfort featuring three charming bedrooms, one bath, streaming TV, and several other amenities. Perfect for six guests, the location is steps away from the Roosevelt bus stop and a ten-minute walk to the Blue line, which will take you to world-class museums, the lakefront, the Magnificent Mile and more.

Superhost

Condo in Wicker Park

4.89 out of 5 average rating, 128 reviews

Luxury Wicker Park Penthouse w/ Private Rooftop

Welcome to my Wicker Park condo! The current photos don’t do it justice. This spacious 2 BR/2 Bath has high ceilings, a newly built huge private rooftop deck, indoor garage space, master bath w jacuzzi, fireplace, washer/dryer, dishwasher, & central air. Come stay in a peaceful, quiet place while still being just a 3 min walk from great food, bars, coffee shops, shopping & green space. 6 min walk to the Damen EL. (Blue line, same as O'Hare airport, and 5 stops from the loop).

Guest favourite

Condo in West Town

4.98 out of 5 average rating, 167 reviews

Spacious 4 Bedroom Condo

Located in West Town in the heart of Noble Square, just north of West Loop with access to all the best restaurants and only minutes away from River North and Old town, enjoy this 4 bedroom, 3.5 bath condo with private parking, 2 living spaces, heated floors throughout the entire lower level and steam showers. A gourmet kitchen stocked with everything you will need including an espresso maker. This home is perfect for families, couples, friends or traveling for business.

Guest favourite

Condo in Skokie

4.91 out of 5 average rating, 109 reviews

Parking Terrace Near Universities Up to 20%OFF

LUXURIES 2 BEDROOMS, 1 BATH APARTMENT WITH LARGE FURNISHED BALCONY. FREE PARKING NEXT TO THE ENTRANCE. BRIGHT & SUNNY SOUTHWESTERN EXPOSURE. LOCATED ON THE FIRST FLOOR-FEW STEPS UP. QUIET PROPERTY IN RESIDENTIAL AREA. MODERN KITCHEN WITH NEW APPLIANCES. KEURIG COFFEE MAKER. CENTRAL AIR & HEATING, HARDWOOD FLOORS, FAST WI-FI INTERNET, LARGE 55" ROKU TV, FREE LAUNDRY. SPARKLING CLEAN APARTMENT. BOOK IT WITH CONFIDENCE YOU WILL ENJOY STAYING HERE, I PROMISE YOU.

Guest favourite

Condo in North Side

4.92 out of 5 average rating, 349 reviews

Susie's Space. 2BR easy parking & pet friendly

Sunny and spacious, 2 bedroom apartment in Avondale near the Green Exchange/ Greenhouse Loft Flexible, self check-in Easy street parking (with provided permits) Pet fee $80 per pet Bedroom 1 with a king sized bed Bedroom 2 with a full bed Air conditioning and ceiling fans Soft linens and towels Separate dining room Fully equipped kitchen Free WIFI Smart TV for streaming Garden in back with a fire pit and charcoal grill Laundry room in basement

Superhost

Condo in River West

4.75 out of 5 average rating, 150 reviews

Cabin 103 at 747 Lofts

This studio apartment is in the perfect location in Chicago for getting to Downtown via the Blue Line L or to the Hot West Loop and Randolph street restaurant row. Walk to bars, shops, restaurants, coffee liquor stores and transportation with ease! You will love our spa baths, in unit laundry and full modern kitchens to make it feel like a home away from home. One of the best pizza spots in Chicago is only steps away!

Guest favourite

Condo in Wicker Park

4.95 out of 5 average rating, 109 reviews

Modern Izakaya Studio in Wicker Park

Stay in a sleek underground izakaya themed studio in one of Chicago's most desirable neighborhoods. Relax and enjoy the quiet zen decor. Find our hidden Japanese whisky room. Kick back in our pillowy loungers and dig into our ramen selection... The Izakaya Studio in the heart of Wicker Park is about giving you a uniquely luxurious guest experience from which to begin your adventures in Chicago.

Superhost

Condo in Hermosa

4.84 out of 5 average rating, 201 reviews

3D Tour! Designer Condo near Logan Square

Scan QR code in photos for a 3D Tour! What you’ll love: - Totally renovated garden unit, completed in 2021. Everything new. - Upscale furnishings & decor. - Gourmet, fully equipped kitchen w/ new appliances, coffee maker and spices. - Remote work station w/ super fast Wi-Fi (600mb). - Serta queen mattress in master. - Bunk beds w/ full and twin sized memory foam mattresses. - Heat & A/C.

Guest favourite

Condo in Oak Park

4.94 out of 5 average rating, 247 reviews

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.

Superhost

Condo in Oak Park

4.79 out of 5 average rating, 353 reviews

Peaceful Oak Park Condo Next to Green Line Metro

Very private, quiet space amidst the activity of Downtown Oak Park. The layout of the space is ideal, as bedrooms are at one end, and the living space is at the other. Private outdoor deck. Oak Park is a beautiful neighborhood full of great places to eat, drink, and shop. Metro and Green line is steps away which means access to anywhere in the city of Chicago. Private parking too!