
Condo vacation rentals in Oak Park
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Top-rated condo rentals in Oak Park
Guests agree: these condos are highly rated for location, cleanliness, and more.

3-bedroom exposed brick in Chicago's Wicker Park
Welcome to Wicker Park - one of Chicago's coolest walkable neighborhoods with endless restaurants, bars & shops. 2 blocks from the famous "L" train with access to the city & O'Hare airport. This 1893 vintage apartment has been freshly renovated and professionally designed blending historic details with a clean and modern aesthetic. The instagrammable one of a kind space has beautiful hardwood floors, soaring 10ft ceilings, exposed brick in all rooms, curated decor and a cozy private deck.

Chic Wicker Park Flat • Near Blue Line
Our stylish 2B/2B Wicker Park condo is perfect for families, event-goers, and business travelers seeking comfort and convenience. Enjoy a mature, elegant, and modern space 5min walk to Damen Blue Line. This private, newly condo features luxury upgrades throughout — a Wolf gas range, Sub-Zero double refrigerator & premium appliances! On Wolcott Ave btwn Milwaukee & Division, you’re steps from top restaurants, boutiques, and everything Wicker Park has to offer. Registration #: R20000058371

Apartment in Clarendon Hills.
Newly renovated Suite in multi family home in Clarendon Hills. Main level: fully equipped kitchen/island, dining area, living room & family room with fireplace. Upper level: Bedroom 1 - king size bed, walk in closet, private bathroom/shower. Bedroom 2 - queen bed, closet. Bedroom 3 - size bed, closet. Living room has a pull-out sofa bed. Family room with gas fireplace, access to deck/outdoor area. Easy access to restaurants, shopping (Oak Brook Mall minutes away), Metra, O’Hare.

RockStar Pad W3A BoysTown/Wrigley Field/Parking lot
HAVE IT ALL @ W3A Chicago Wrigley Field/Boystown/Lakeview -Newly renovated like new in safe centrally located East Lakeview. -10 min walk to Wrigley Field, Boys town, beaches, super markets, restaurants with late night dining. 5 min walk to Metro Sheridan Red Line (direct downtown), private enclosed parking $10/night & or free permits for street parking -600 thread count linens, fluffy soft pillows, house coats, high speed WiFi, Sonos speakers, stylish design & in unit washer & dryer

Urban Luxury 1BR/2BA Logan Square Condo w/Garage
Luxurious 1BR/2BA garden-level condo in vibrant Logan Square! Comfortably furnished with tons of light and amenities, conveniently located one block from the Logan Square Blue Line Station and located on a quiet street. Steps from all of the hip restaurants and nightlife in Logan Square. Huge back yard and patio with fire pit for guest use. Free on-site garage parking with remote. And, if using public transit, the Logan Square is 8 stops, ~15-20 minutes from the Loop downtown!

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 Belmont 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.

Modern/Spacious 2BR/2BA West Town
Light, airy and luxurious, our duplex has a self-contained, 1400 sq. ft. 2nd floor with a private street entrance. There are two bedrooms and two baths. The master bedroom has a fireplace, a private balcony and a huge bathroom ensuite. In addition there is a dining room and living room. Minimal kitchen facilities include small fridge and micro. Easy commute downtown- 20 by car, 25 by bike and 30-40 minutes via public transportation. Close to hwy and public trans.

Spacious 3BR • Great for Groups • Fast WiFi • Pets
This pet-friendly, Logan Square apartment is brimming with details to make your stay feel like a home away from home. All 3 bedrooms boast super-comfy queen beds with an abundance of pillows and lots of storage space for your belongings. The third bedroom is made private by a lush velvet curtain. There are two dedicated workspaces in the apartment for your work-from-anywhere lifestyle needs. A very well-appointed kitchen is begging for home-cooked meals.

Chic Home! Walk to Nightlife-Comedy-Restaurants!
Stay in the heart of Chicago Old Town! This bright, cool and comfortable one bedroom, one bath is decked out in mid century modern furniture, exposed brick, new appliances and has a true city feeling! It comfortably sleeps two (3rd person can sleep on the couch), just 2 blocks to Lincoln Park, and 3 blocks to the famous Second City & stellar Old Town bars. Not to mention a quick 5 minute Uber ride to river north district (downtown Chicago)!

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.

Designer Loft in Fulton Market with Parking
Discover our spacious, two-level modern loft, perfect for business travelers. Featuring sky-high ceilings, floor-to-ceiling windows, and a newly renovated private terrace with a fire pit. Located in the heart of Restaurant Row, just two minutes from downtown. Enjoy a luxury stay with one dedicated parking spot included. Ideal for solo travelers or couples seeking a stylish urban retreat.

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!
Popular amenities for Oak Park condo rentals
Weekly condo rentals

Chic and Charming Vintage Condominium in Lincoln Park

Cozy Apartment with Free On-Site Parking

Lincoln Square Gem!

NEW luxury Old Town 1-Bedroom condo

Modern Chicago Movie Themed Apt

Near Lake Michigan & Wrigley Field

Marvelous Condo w/ Pri Prkng Cls to Transit &Beach

Remodeled Duplex in the Heart of Lincoln Park
Pet-friendly condo rentals

of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D

Cozy Lincoln Park Condo near the lake.

Spacious 3BR/3BA Condo in Trendy Ukrainian Village

Studio flat in the heart of Chicago's Gold Coast

Convenient & Spacious 3BR Condo w/Free Parking

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!

Susie's Space. 2BR easy parking & pet friendly
Condo rentals with a pool

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

Just remodeled apartment close to airport and mall

Smoke & Pet Free, Washer Dryer, Fireplace, Balcony

Chicago's Treasure "Heart of Evanston" 2bdr +1 Ba

Pond View, Washer Dryer, Non Smoking Community

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool

Iconic Style, Charming Lake View
When is the best time to visit Oak Park?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $160 CAD | $195 CAD | $186 CAD | $223 CAD | $208 CAD | $243 CAD | $235 CAD | $245 CAD | $212 CAD | $212 CAD | $209 CAD | $197 CAD |
| Avg. temp | -3 °C | -1 °C | 4 °C | 10 °C | 16 °C | 22 °C | 25 °C | 24 °C | 20 °C | 13 °C | 6 °C | 0 °C |
Quick stats about condo rentals in Oak Park

Total vacation rentals
Explore 20 vacation rentals in Oak Park

Nightly prices starting at
Oak Park vacation rentals start at $82 CAD per night before taxes and fees

Verified guest reviews
Over 2,070 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Oak Park vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Oak Park rentals

4.8 Average rating
Oak Park stays are highly rated by guests—averaging 4.8 out of 5!
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- 875 North Michigan Avenue
- Soldier Field
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- The Field Museum
- Wicker Park
- Wilmot Mountain Ski Resort
- Lincoln Park Zoo
- Garfield Park Conservatory
- Oak Street Beach
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Willis Tower
- Illinois Beach State Park
- Washington Park Zoo
- University of Chicago




