Best Vacation Rentals in Oak Park

Historic Oak Park Home for 6 / Hemingway District offers accommodations in Oak Park, 7 miles from United Center and 8.7 miles from Union Station. This apartment offers free private parking, a 24-hour front desk, and free Wifi. 360 Chicago is 10 miles away and Willis Tower is 10 miles from the apartment. The apartment features 3 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 1 bathroom with a hair dryer. Towels and bed linen are offered in the apartment. For added privacy, the accommodation features a private entrance. You can play billiards at Historic Oak Park Home for 6 / Hemingway District. Shops at Northbridge is 10 miles from the accommodation, while Water Tower Chicago is 10 miles from the property. Chicago O'Hare International Airport is 8.7 miles away.

- "Fantastic place to stay and we were welcomed very warmly by the hosts!" - "Oak Park Illinois apartment - Perfect" - "Nice worthy comfortable stay" - "Clean, well kept and comfortable apartment for 6, with a central Oak Park location." - "A perfect short stay in a beautiful historic home." - "Great! Hosts were super responsive too!" - "Don't touch that dial!"

Bed & breakfast in Oak Park with free breakfast and a hot tub
This smoke-free bed & breakfast features a snack bar/deli, a hot tub, and a business center. Free breakfast, free WiFi in public areas, and free self parking are also provided. Other amenities include conference space, a computer station, and a library.
Harvey House Bed & Breakfast offers 5 air-conditioned accommodations with DVD players and bathrobes. Each accommodation is individually decorated. Cable television is provided.

Bathrooms include showers, slippers, and hair dryers. This Oak Park bed & breakfast provides complimentary wireless Internet access. Housekeeping is provided daily.

- "Beth and staff are wonderful. Beautiful accommodations. Access to front porch swing and back patio with gas fireplace and ample dining and living space on main floor to enjoy your breakfast." - "Another amazingly relaxing stay at the Harvey House! Highly recommend it." - "Great location, restful accommodation with lots of beautiful touches. Very welcoming host with excellent communication. " - "Outstanding in every way. A true 5 star experience."

Lovely vintage Oak Park 3bd 1ba perfectly located near public transit & Chicago is a recently renovated apartment in Oak Park where guests can make the most of the garden and barbecue facilities. The air-conditioned accommodation is 6.5 miles from United Center. There's an outdoor fireplace and guests can use free Wifi and free private parking. Providing a patio with garden views, this apartment also provides guests with a flat-screen TV, a well-equipped kitchen with an oven, a microwave, and a toaster, as well as 1 bathroom with a walk-in shower and a hair dryer. For added privacy, the accommodation has a private entrance and is protected by full-day security. The apartment has a picnic area where you can spend the day outdoors. Water Tower Chicago is 8.3 miles from the apartment, while Willis Tower is 8.6 miles away. Midway International Airport is 6.8 miles from the property.

- "A wonderful Chicago experience." - "This place is so cool! ,beautiful ,clean functional and good location ,We’re love all" - "Clean, beautiful setup!" - "BEAUTIFUL, CLEAN, SAFE" - "Relaxing, comfortable, gorgeous home for our family." - "booking.com has system issues. However, the host was very accessible and accommodating." - "Host was simply delightful. Would definitely return." - "Nice place but beware of price switches"

Suburban hotel with 2 restaurants and bars
Along with 2 restaurants, this smoke-free hotel has 2 bars/lounges and a fitness center. Free WiFi in public areas and free self parking are also provided. Additionally, a business center, conference space, and concierge services are onsite.
Carleton of Oak Park offers 153 accommodations with coffee/tea makers and complimentary weekday newspapers. Beds feature pillowtop mattresses. LCD televisions come with premium cable channels. Accommodations at this 3-star hotel have kitchenettes with refrigerators and microwaves. Bathrooms include bathtubs or showers, complimentary toiletries, and hair dryers.

Guests can surf the web using the complimentary wireless Internet access. Business-friendly amenities include desks and phones. Additionally, rooms include irons/ironing boards and blackout drapes/curtains. Housekeeping is offered daily and hypo-allergenic bedding can be requested.

- "Only elevator was broken last day" - "good" - "The staff were very friendly, helpful, happy." - "This was the perfect place to stay. Restaurants, CTA, grocery stores, parks, shopping, and family all in walking distance. The hotel consists of 3 different buildings: The main Carleton and the Plaza Hotel are joined and there is a separate motor lodge. We had a king in the Plaza. The room was spacious with a small kitchenette (microwave, refrigerator, pod coffee maker, dishes and utensils). The bed was incredibly comfortable. There’s also 2 restaurants - fancy Italian and basic pub - on ground floor that you can charge to the room."

Gallery Loft of Oak Park #1 Top Host in IL is located in Oak Park, just 7 miles from United Center and 9.1 miles from Willis Tower. This apartment offers air-conditioned accommodations with a terrace. The property provides a children's playground and parking on-site. With free Wifi, this 1-bedroom apartment features a satellite flat-screen TV and a kitchen with an oven and microwave. Towels and bed linen are available in the apartment. For added privacy, the accommodation features a private entrance. You can play tennis at the apartment. Union Station is 9.1 miles from Gallery Loft of Oak Park #1 Top Host in IL, while DePaul University is 9.2 miles from the property. Midway International Airport is 6.8 miles away.

- "Perfect stay!" - "Unique loft apartment with good amenities in a great location" - "A great place to stay in Oak Park"

Located in Oak Park, this welcoming apartment brings it all within your reach. Thanks to the convenient onsite parking, you can either leave your vehicle behind and enjoy a short 5-minute walk to Frank Lloyd Wright Historic District, or easily tackle the 12-minute drive to United Center. Check out other neighborhoods and see more of Oak Park by hopping on a metro at Oak Park Station (Green Line), just a short 9-minute walk away.

This 3-bedroom, 1-bathroom rental features a computer station and multilingual staff. Enjoy the free WiFi and pool table.

- "Very lovely home. Clean and great communication. One drawback is that the property only comes with 1 bathroom. " - "Beautiful property in a convenient location. Only hiccup was that I didn’t receive the code for the door by check in, and had to call, but that was resolved quickly. Amenities such as soaps, towels, and dishes were well stocked, and we really enjoyed the mini pool table. We also felt very secure, with our car in the garage. Would definitely come back!"

Historic Oakpark Home offers accommodations in Samuel A Rothermel Houses, 7 miles from United Center and 8.7 miles from Union Station. This apartment offers air-conditioned accommodations with a patio and free Wifi. 360 Chicago is 10 miles from the apartment and Willis Tower is 10 miles away. The apartment features 3 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 1 bathroom with a hair dryer. Towels and bed linen are offered in the apartment. The accommodation is non-smoking. Shops at Northbridge is 10 miles from Historic Oakpark Home, while Water Tower Chicago is 10 miles from the property. Chicago O'Hare International Airport is 8.7 miles away.

- "we couldn’t have been more pleased & will definitely stay again" - "Best location" - "Charming, large apartment in a terrific location for Oak Park and Chicago"

Summary:
This Arts District located beautiful Retro Cottage 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.

The Space:
Looking forward to hosting you at this Bright, Charming & Clean 2 bedroom – 1 bathroom Retro Cottage with private front yard! The entire location has been renovated but also has the charm and vibe of an older home. This location has all you need for a comfortable stay-onsite laundry, fully equipped kitchen (gas stove and oven) and 2 FREE parking spaces in the rear driveway!

• Bathroom - Tub/shower combination (half the size of a normal tub). For your stay we provide shampoo, conditioner, body wash, hair dryer and fresh towels.

• Bedroom 1 - Queen size bed - Ceiling fan and floor fan with cooling capabilities provided in this room. You can leave the door open for window AC of living room to cool you down as well.

• Bedroom 2 - Two twin size beds- second twin bed is a trundle bed. Window AC unit in this room.

• Radiant heat and window air conditioning (two AC units- one in 2nd bedroom and one in the living room area, it is enough to cool the entire unit if left on high cool setting)

• Free parking for two vehicles in our private driveway in back of our property. Please note: there is no access by car in the front of the property, access is through the alley.

• High speed internet

• Laundry in-unit and free

• Toaster, Microwave & Blender

• Private front lawn and patio with bistro lights

• 2 free parking spots in driveway directly behind home

• Fully stocked kitchen with plenty of pots and pans, chef knives, cooking utensils, cups, plates, coffee and tea mugs and wine glasses which makes this a great place for a long-term stay

• Window Air Conditioning in one bedroom and living room and ceiling fan and floor fan in other bedroom to keep you cool in the summers.

• Fully stocked bathroom with lovely hand soap, shampoo, conditioner, body wash, full-size hair dryer and nice, soft, luxury towels.

• Living room offers a sofa that doubles as a futon for your convenience

• 4K 55in Smart TV

• 5 min walk to L Blue line train to take to downtown Chicago

Also this location is:

• 5min drive to Grocery Store
• 5min walk to Buzz Cafe
• 4min to Mills Park or Randolph Tot Lot for the entire family
• 15min to downtown Chicago and see The Bean, Mag Mile on Michigan Ave
• 4- 5mins to nearby restaurants, gyms, boutiques, bars, and farmers markets.

Guest Access:
You will have access to the entire property.

The Neighborhood:
Located just 5 mins to the L train in downtown Oak Park, Frank Lloyd Wright Home/Studio, Ernest Hemingway Museum, as are shops, dining and entertainment. The iconic Bean, Willis Tower, in Chicago is a mere 15 min drive away. This location offers Free parking, fast WiFi, fully stocked kitchen, and multiple sleeping spaces that accommodates a maximum of 5 friends or family members in a beautiful tree line quiet residential neighborhood.

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.

Getting Around:
Uber, rental car and L train are all easy and great ways to get around the city!

Other Things to Note:
***Please read our house rules and nuances with the home prior to booking

*** OCCUPANCY LIMIT IS 5 - NO VISITORS ALLOWED

***Person booking must be 21 years or older. No third party bookings please. Per Airbnb regulations, the person making the reservation must be one of the guests for the entire stay.

***We want to make sure that your stay exceeds your expectations. When booking or submitting a booking request, please tell us about yourselves, your interest in our home and indicate that you have read the full listing and house rules, thank you!!!

***Property is equipped with cameras that record all motion in its range. All cameras are on exterior of property. There are no recording devices inside the home.

Interaction with Guests:
Welcome to your home away from home! I am available for any questions or feedback you may have. Please contact me through the App and I will do all I can to best assist you! I am here to make sure your stay is relaxing and enjoyable!

- "The cottage was as advertised and served as a great home-base for a birthday weekend spent biking around greater Chicago with a friend in celebration of our birthdays. Great communication with the owner and the cottage had everything we needed." - "I could not have asked for an easier spot in order to get to downtown Oak Park (5 minute Uber), train access to downtown Chicago (1 minute walk) and breakfast right around the corner. As high traffic as it might sound there was essentially no residual noise from any of it. Quiet, clean and cozy. I highly recommend this cottage!"

Historic Oak Park Residence offers accommodations in Oak Park, 7 miles from United Center and 8.7 miles from Union Station. This apartment offers air-conditioned accommodations with a patio and free Wifi. 360 Chicago is 10 miles away and Willis Tower is 10 miles from the apartment. The apartment features 4 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 1 bathroom with a hair dryer. Towels and bed linen are offered in the apartment. The accommodation is non-smoking. Shops at Northbridge is 10 miles from Historic Oak Park Residence, while Water Tower Chicago is 10 miles from the property. Chicago O'Hare International Airport is 8.7 miles away.

- "Oak Park is a great community, close to places we frequent."

Close to birdwatching, this smoke-free apartment brings it all within reach. Frank Lloyd Wright Historic District is just a short walk away, so you can leave your car at the property, which offers onsite parking, or jump in your vehicle to make the 12-minute drive to United Center. Check out other neighborhoods and see more of Oak Park by hopping on a metro at Oak Park Station (Green Line), just a short 10-minute walk away.

As you settle into this 4-bedroom, 1-bathroom rental, you'll find a computer station and multilingual staff. Enjoy the free WiFi and TV.

- "We absolutely loved our stay at Historic Oak Park residence! The apartment was amazing and the hosts had prepared the room for our kids in a very thoughtful way. Close to restaurants and about 10-15min walk to the green line that heads to central Chicago. Would love to stay there again next time in Chicago." - "This was quite a charming home. The access to public transportation was great. One mile walk or drive to parking garage. We ventured into the city every day but could have easily stayed in Oak Park."

Oak Park 5bd 2bth sleeps 11 with 3 private parking is located in Oak Park, just 8 miles from Union Station and 8.2 miles from Water Tower Chicago. The property is around 8.4 miles from 360 Chicago, 8.8 miles from Shops at Northbridge, and 9.4 miles from Willis Tower. Free Wifi is available throughout the property and United Center is 6.3 miles away. The air-conditioned vacation home is composed of 5 separate bedrooms, a living room, a fully equipped kitchen with a dishwasher and oven, and 2 bathrooms. A TV is offered. The accommodation is non-smoking. DePaul University is 10 miles from the vacation home, while CIBC Theatre is 10 miles from the property. Midway International Airport is 7.5 miles away.

Security/Safety • Pet Friendly • Internet • Air Conditioner • Child Friendly • Fireplace/Heating

Nestled in Oak Park, this 2-bedroom, 1-bathroom apartment brings it all within your reach. Fans of nature and the outdoors will love being 19 minutes by car from Lake Michigan and 16 minutes from Millennium Park. Frank Lloyd Wright Historic District is just a short walk away, so you can leave your car at the property, which offers onsite parking, or jump in your vehicle to make the 12-minute drive to United Center. Check out other neighborhoods and see more of Oak Park by hopping on a metro at Oak Park Station (Green Line), just a short 10-minute walk away.

While you're here, you can enjoy all the comforts of home and more, including free WiFi and a garden, as well as laundry facilities and multilingual staff.

- "We had a great time at Oak Park. The host was very accommodating,giving us good places to eat. The place was very clean. I'd would go there again." - "This apartment was is so cute! Hosts were awesome." - "Good location, nice neighborhood, restaurants close" - "Beautiful accommodation, tastefully furnished to a high standard, cozy and comfortable. Our host Kettil was easily contactable and answered our questions in a timely manner enabling us to get on with our plans. The only issue and it was a minor one , is that there are 3 flights of stairs to get to the door to the loft and with large cases it was a little awkward. However this did not detract from our wonderful stay at this accommodation. "

Less than 5 minutes’ walk from CTA Green Line trains and the Oak Park Metra station, this historic hotel features guest rooms with flat-screen TVs and free Wi-Fi. The hotel boasts 2 restaurants on site. A microwave and a refrigerator are included in all rooms at Carleton of Oak Park. A work desk and a hairdryer are also provided in each guest room. Complimentary access to an off-site fitness centre, less than 5 minutes’ walk from the property, is offered to all guests. A launderette and dry cleaning service are available on site at Oak Park Carleton. Free parking is provided to all guests. Barclay´s American Grille, located just off the main lobby, features classic American cuisine in a relaxed and casual atmosphere. Poor Phil´s Restaurant, located on the first floor of the Carleton, is serves breakfast, lunch and dinner daily. Chicago city centre is 10 miles from this hotel. The birthplace of Ernest Hemingway is less than 5 minutes’ drive from the property.

Parking • Breakfast • Internet • Air Conditioner • Wheelchair Accessible • Child Friendly

Close to birdwatching, this smoke-free apartment brings it all within reach. Enjoy a short 5-minute walk to Frank Lloyd Wright Historic District or easily tackle the 12-minute drive to United Center. If you're looking to expand your horizons and see other nearby locales, you can catch a train at Oak Park Station, a short 14-minute walk away.

This 3-bedroom, 1-bathroom rental features a computer station and multilingual staff.

- "A lot of space!" - "We stayed here on a weekend mini vacation because my son had a college volleyball game nearby. The home was pristine and very cozy. Close to so many restaurants and rich in history. We loved the original hard wood flooring and overall atmosphere. 10 out of 10 recommend! Although we stayed in the winter so walking wasnt our choice of transportation we had a couple issues with parking, primarily bec we arent used to city lifestyle, that was the only difficulty that occured."

Harvey House Bed & Breakfast provides air-conditioned rooms in Oak Park. Both free Wifi and parking on-site are available at the bed and breakfast free of charge. Shops at Northbridge is 8.9 miles away, and Willis Tower is 9.4 miles from the bed and breakfast. Harvey House Bed & Breakfast offers a flat-screen TV and a private bathroom with bathrobes, slippers, and a bath or shower. The rooms are equipped with heating facilities. There is an on-site snack bar. The bed and breakfast has a picnic area where you can spend the day outdoors. United Center is 7.4 miles from the accommodation, while Water Tower Chicago is 8.9 miles away. Midway International Airport is 8.1 miles from the property.

- "comfortable and extremely pleasant."

Relax in comfort in this 1-bedroom 2nd floor apartment located in Historic village of Oak Park. Impeccably restored, the space is styled with mcm furnishings and has updated amenities. A king bed in the bedroom and a cozy futon in the living room, offer sleeping arrangements for up to four. The bathroom features a walk-in shower, beautiful tile work, hairdryer, soaps and toiletries for convenience. This art-filled space also includes amenities like WiFi, heating, and AC. Labeled a "Chicagoland gem" by many returning guests, the apartment is near the birthplace of Ernest Hemingway, Frank Lloyd Wright Home/Studio. The apartment features gallery walls by local artists, including the hosts original artwork. Walking distance to live music (Fitzgerald's, Friendly Music Community), and restaurants. Easy street parking and kitchen well stocked. Private porch. Perfect for long and short term stays.

Host, Lacy Coligan was the #1 Top New Host in Illinois in 2021, https://news.airbnb.com/the-number-one-new-host-in-each-us-state/

- "Really cute place with a great loft balcony. Cool, vintage vibe. Awesome neighborhood."

Housed in a historic building, the recently renovated The Oak Park Loft offers accommodations with a tennis court and free Wifi. Housed in a building dating from 19th century, this apartment is 6.8 miles from United Center and 10 miles from Shops at Northbridge. The accommodation provides a 24-hour front desk. Providing access to a patio, the apartment consists of 2 bedrooms. The air-conditioned apartment also features a flat-screen TV, a fully equipped kitchenette with a fridge, a seating area, washing machine, and 1 bathroom with a shower. The apartment offers bed linen, towels, and laundry service. Guests at the apartment will be able to enjoy activities in and around Oak Park, like cycling. Water Tower Chicago is 10 miles from The Oak Park Loft, while Union Station is 10 miles from the property. Chicago O'Hare International Airport is 8.7 miles away.

- "Comfortable, convenient, and clean - definitely a winner!" - "Wonderful!" - "I would recommend this and stay there again.k"

Our comfy, newly remodeled garden unit is 3 blocks to the train with free parking in upscale, safe, walkable Oak Park. Enjoy some time in our little urban farm. Check out the gardens and visit our 4 friendly hens. This non-smoking studio with a kitchenette is perfect for tourists, families, or business travelers. We require no check-out chores. Easy highway and airport access.

No parties or additional guests allowed. Minimum age to book is 25.

Visit my profile for additional units.

We hope you will enjoy our newly remodeled garden apartment. We have worked hard to ensure that our 700 square foot open concept studio is comfortable, clean, cute and supplied with all the basic necessities. We are happy to be able to offer you plush mattresses, plentiful blankets and pillows, and cozy cotton sheets.

- "Fabulous place to stay with easy access to Chicago." - "What a clean convenient location! The studio was so clean, comfortable and quiet!! We easily took am Uber to The Fitzgerald for a music festival and returning to a comfortable place topped off our day! I highly recommend this place and we hope to be back!! Owners were so welcoming and helpful! Truly a 10 star stay!!"

Classic Oak Park Home, 11 Mi to Downtown Chicago! offers accommodations in Oak Park, 8.7 miles from Union Station and 10 miles from Shops at Northbridge. Guests staying at this vacation home have access to a patio. Free Wifi is available throughout the property and United Center is 7 miles away. The air-conditioned vacation home consists of 4 bedrooms, 2 living rooms, a fully equipped kitchen with a dishwasher and a coffee machine, and 2 bathrooms with a bath and a hair dryer. Towels and bed linen are offered in the vacation home. The property has an outdoor dining area. Water Tower Chicago is 10 miles from the vacation home, while Willis Tower is 10 miles from the property. Chicago O'Hare International Airport is 8.7 miles away.

- "Very comfortable for short stay. The home is lovely. Thank you"

This gorgeous 2bed/2bath packs a powerful punch, and more amenities than you'll know what to do with.
-1 Private Parking Spot directly behind the building.
-super-fast Wi-Fi
-Shared laundry near unit.
-Stainless-steel appliances and a fully stocked kitchen with plenty of cookware which makes this a great place for a long-term stay!
-One of the two bedrooms has a king bed, 2 extra large walk in closets, with a rollaway bed, air conditioning, a ceiling fan, and an en suite bathroom that gives a private oasis and luxury experience.
-Guests bedroom has two full size beds, with, a large walk in closet, guests bathroom, air conditioning and a ceiling fan.
- Baby high chair
-Baby spoons
-Baby bowls
- Portable crib
-Baby cups
- Rollaway bed
All our furniture is stylish and brand new, sheets, comforters, and pillows are of the highest quality with a regular couch that makes this a great accommodation for up to six guests.
-We also invested in premium pillows of different firmness and style in order to ensure a quality sleep. -4K Smart tv that provides ample streaming services watch all your favorite shows for the entire family
-Complimentary, Brita water jug along with bottles of water, regular and decaf coffee, tea, creamer and sugar.
-Fully equipped kitchen with plenty of pots and pans, chef knives, cooking utensils, cups, plates, wine glasses, baking pans, waffle maker, rice maker, slow cooker to cook gourmet meals for the entire family. -cozy living room with multiple family fun board and card games that make this space perfect for family gatherings.
-Iron and ironing board.
-blackout blinds
-Bathrooms equipped with lovely hand soap, shampoo, conditioner, body wash, full-size hair dryer and abundance of huge, soft, luxury towels.
Expectations staying in a condo/apartment building.

*******To access the building and the apartment, there are a few steps to get to the apartment. This is a first-floor apartment. **********

*****Vacationing in a condo building like any shared building, has its
uncontrollable elements.

Noises from other tenants in the community. They’re lots of working professionals that are leaving home at different times throughout the day, so you
might hear a little noise. Understand that our Quiet hour time frame is only for this apartment not for the entire building.****

-8min drive and park at the CTA Blue line train to take to downtown Chicago

-6min drive and park to CTA Harlem and Lake Green line train to take to downtown Chicago

-6min drive to downtown Oak Park’s Classic Lake Street Theatre

-4min drive to Scoville Park

-9min drive to Dominican University

-15min drive to downtown Chicago

Nearby restaurants, gyms, parks with playgrounds, boutiques, grocery stores, bars, and farmers markets.

Come stay and play in the heart of downtown Oak Park all within easy walking distance. This space is large and comfortable.
We strive to make sure that your stay exceeds your expectations and that you would stay again and tell your friends to do the same. Looking forward to hosting you and your families.

- "Everything was clean, well-organized, and easy to find. The directions were spot on, communication from the owner was frequent, but not too much. Awesome stay." - "The stay was amazing and everything was in good condition nothing was wrong with the Place. host always has fast responses to questions or concerns 10/10" - "Perfect and accommodating hosts! Reserved parking spot, cold AC on hot summer days, stocked kitchen supplies abs comfy beds for a perfect location to visit our family in the city (without staying right in the city)."