Condo vacation rentals in Oak Park

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Top-rated condo rentals in Oak Park

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Guest favorite

Condo in West Town

4.94 out of 5 average rating, 136 reviews

711 The Penthouse

Luxurious upscale Duplex Penthouse-River West neighborhood in downtown Chicago! Newly rehabbed and updated interior design that is mind blowing. Over 5600 sq ft. Features 5 bedrooms, 2.5 baths, 3 largeTVs with sonos sound system, game room!!. Near CTA Blue Line, close to the best dining and attractions of Chicago! Two large living areas perfect for hosting small events, bachelor(ette) parties, bridal or baby showers, work/travel, and family reunions. Rooftop with beautiful view of the skyline!

Guest favorite

Condo in East Rogers Park

4.91 out of 5 average rating, 128 reviews

Magnificent Place & A Parking Space

1 Bedroom with 1 bathroom This spacious, quiet condominium is located in the Rogers Park neighborhood of Chicago, 3 minute walk from the local pubs, restaurants, shopping, and tennis court. Great for weekend trips as the beach is a quick bike ride 5 minute bike ride. Metra UP-Northwest, a 17 minute train ride to Downtown Chicago (4 min walk West to catch this train). CTA Morse Red Line Train is also available, making multiple stops on its way Downtown (5 min walk East to catch this train).

Guest favorite

Condo in Bridgeport

4.89 out of 5 average rating, 102 reviews

Convenient & Spacious 3BR Condo w/Free Parking

Get cozy in this spacious 3-bedroom condo, conveniently located 3 blocks from the Halsted Orange Line overlooking Palmisano Park and only 5 minutes' drive to McCormick Place. Clean, neat, modern and comfortable, the condo offers spacious living space with an open kitchen, washer/dryer, and an outdoor balcony perfect for families and groups. Hungry? Our complex offers a few delicious high rated yelp restaurant options to fulfill your appetite. We look forward to hosting you and your guests!

Guest favorite

Condo in Uptown

4.92 out of 5 average rating, 132 reviews

Stunning, Spacious, & Sun-Soaked 2bed Uptown Condo

Welcome to your home away from home in Uptown! My bright and inviting condo offers a perfect blend of comfort and convenience, with your own sunny living room to relax, fully-equipped kitchen and separate dining room, spacious private bedroom, serene sunroom with full bed for extra guests, and a workspace for business travelers. Just steps from the lakefront and Montrose Beach, and a 6-minute walk to the Wilson Red Line, this location is excellent for exploring all that Chicago has to offer.

Guest favorite

Condo in Lake View

4.99 out of 5 average rating, 130 reviews

RockStar Pad W3A BoysTown/Wrigley Field/Parking

HAVE IT ALL @ W3A Boys Town/Wrigley Field/East -Newly renovated/brand new in safe centrally located East Lakeview. -10 min walk from Wrigley Field, Boys town, beaches, super markets restaurants with late night dining. 5 min walk to the Metro Sheridan Red Line (straight shot downtown), 1 free enclosed parking plus free permitted street passes. -600 thread count linens, fluffy soft pillows, house coats, high speed WiFi, Sonos speakers, stylish furnishings & in unit washer and dryer.

Guest favorite

Condo in River North

4.99 out of 5 average rating, 124 reviews

Luxurious River North 3BR/2BA- Free Onsite Parking

Experience an urban oasis unlike any other: - Complimentary parking for one vehicle in our attached lot - Spacious, recently renovated kitchen - Immersive entertainment with large-screen TVs - Unwind with a game of poker or foosball at our dedicated tables - Conveniently located within walking distance of the Magnificent Mile - Surrounded by an array of vibrant bars, restaurants, and nightlife - Embrace our inviting patio Indulge in a memorable stay at our 3rd-floor condo!

Guest favorite

Condo in River North

4.91 out of 5 average rating, 133 reviews

Brilliant Downtown Chicago 3-Bedroom Condominium

Situated in downtown Chicago, right next to the Godfrey Hotel, this spacious and bright 3-bedroom, 2-bathroom condominium is perfectly suited to deliver the best adventures the Windy City has to offer. Our vacation home includes four sleeping areas with 1 King & 3 Queen sized memory foam mattresses and features everything from a fully-stocked kitchen to smart gadgets like Alexa. PARKING: We offer a $30 per day parking credit. This credit pays for most or all parking costs.

Guest favorite

Condo in West Town

5 out of 5 average rating, 137 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 favorite

Condo in Mount Prospect

4.9 out of 5 average rating, 180 reviews

Lovely 3-bedroom condo, free parking, Unite 1

Bring the whole family to this great place with lots of room for fun. Beautiful condo in Mt Prospect, IL. 3 bedrooms, 1 full bath, and half bath. Great location with walking distance to restaurants and shops. Near the train and highway easy access to get to downtown Chicago. Full kitchen with fridge, stove, microwave, dishwasher, coffee maker, washer and dryer. Central heat and ac, security camers. Plenty of free parking on the driveway. Cable TV

Guest favorite

Condo in Uptown

4.98 out of 5 average rating, 244 reviews

Near Lake Michigan & Wrigley Field

Available 2B/2B condo with 2 King Size Beds. One block from the Aragon Ballroom and Riviera with great views of Uptown and two blocks from Lake Michigan. It’s also a perfect place to stay if your in town for a Cubs game. You can see the stadium from the rooftop deck. Walking distance to everything you need, 2 train stations, groceries, gym, restaurants/ bars. The perfect place to come and go as you please with easy key code entry.

Superhost

Condo in Wicker Park

4.83 out of 5 average rating, 328 reviews

Lively Wicker Park 2br, Steps to Damen Blue Line

Rehabbed 2BR 1BA garden unit in the very popular neighborhood of Wicker Park/Bucktown! 2 queen beds and full of amenities. Just a block from everything this neighborhood has to offer and 2 blocks from the 'L' to take you downtown or to O'hare Airport. Premium location to effortlessly walk from our quiet side street and be in the heart of all the entertainment! I provide all the essentials to make your stay easy and comfortable!

Guest favorite

Condo in River North

4.98 out of 5 average rating, 127 reviews

City Center Oasis: 3BR/2BA✔︎ Patio✔︎ Parking(2x) ✔︎

Perfectly in the heart of Chicago in the River North neighborhood. You will experience Chicago easily from here! • Free parking (2) in our attached lot! • Surrounded by world class shopping on the Magnificent Mile • In the heart of the city's best dining and walking to big-city nightlife • Walk to Lake Michigan and Navy Pier • Steps from the local trains and buses to reach the outer parts of the city