Condo vacation rentals in Northwest Side

Find and book unique condos on Airbnb

Top-rated condo rentals in Northwest Side

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Guest favourite

Condo in Chicago

4.84 out of 5 average rating, 304 reviews

Peaceful & Airy Modern-Chic Condo in Trendy Pilsen

Brand New Private Modern 2 bd 2bth apt for your stay in Chicago. We are located 2 blocks form the CTA line in the heart of Pilsen, a neighborhood Time Out labeled the 10th coolest in the world. Newly renovated, hardwood tiled floors throughout, chefs kitchen, toiletries, brand new furnishings including 2 queen beds, 1 twin sleeper, fresh linen, smart TV (HBO, Netflix, Hulu) wifi, tons of books,coloring books,board games & puzzles! We truly want you to feel like this is your home away from home.

Jan. 26 – Feb. 2

$228 CAD per night

Guest favourite

Condo in Chicago

4.91 out of 5 average rating, 121 reviews

Spacious & Modern Family Friendly North Center Apt

Newly renovated, modern kitchen & bath, solar-powered, comfortable beds. Great location in safe neighborhood, Jewel Grocery store, Trader Joe’s, craft breweries, restaurants, bars, Wrigley Field nearby & brown line train to downtown Loop. Families with children are welcome. Owners with 2 young kids live upstairs, we are available to address guest needs. No smoking anything on property. Parties & excessive noise prohibited, max of 6 people allowed inside at anytime. Quiet hours 11 pm - 8 am.

Nov. 2 – 9

$294 CAD per night

Guest favourite

Condo in Chicago

4.93 out of 5 average rating, 187 reviews

Pvt 1bdr Rogers Park, Loyola, Northwestern.

Visiting Northwestern, Loyola University, Rogers Park or North Shore Evanston Hospital? This AirBnb is perfectly situated. An immaculately clean, private apartment 2 blocks from parks & sand beaches, walking distance to Loyola, short ride to Northwestern, steps to public transportation - red line "El" trains & bus routes. Apt has a private, queen bedroom with en suite full bathroom, living room with queen sofa bed, TV, dining table and kitchenette. Dogs allowed and Parking available for a fee.

Dec. 26 – Jan. 2

$193 CAD per night

Guest favourite

Condo in Chicago

4.88 out of 5 average rating, 235 reviews

2 King Bed Condo Easy Downtown Free Street Parking

Welcome to your private home away from home in Ukrainian Village, a Top 10 neighborhood in the nation! Our super comfy 2 King Serta pillowtop mattress in the garden (lower) level condominium with everything you need during your stay and more. We have been told over & over the photos do not do this place justice. Walk to a wide variety of award winning restaurants, hip shopping/coffee shops, grocery, public transport, bars and more! A quiet neighborhood with quick access to all Chicago offers!

Sep. 13 – 20

$279 CAD per night

Guest favourite

Condo in Chicago

4.97 out of 5 average rating, 100 reviews

Stylish 3BR + Free Parking 10-15mins from Downtown

This apartment is located in Historical Humboldt Park, a residential area that is an easy 10-15mins drive to Downtown, Medical District, Wicker Park, West Town, Logan Square, and Ukranian Village. Due to the proximity, we host guests visiting for tourism, fests,concerts, sport events , work conferences, weddings, birthdays, and visiting family. There are grocery stores closeby. There’s street parking and a gated private parking available. Location wise, you are close enough to everything.

Sep. 3 – 10

$279 CAD per night

Superhost

Condo in East Garfield Park

4.9 out of 5 average rating, 136 reviews

East Garfield Park 2 Bedroom

Charming two bedroom, two bath Apartment. With washer/dryer.in Historic East Garfield Park beautiful block filled with old Mansions. Half a block to the Green line El Train.3 stops to Morgan street also known as the fulton market district and resturant row.5 stops to Downtown Chicago. Half a block from Garfield Park and it's Conservatory. Carroll street Artist district 3 blocks away Ukrainian. village, Logan square, wicker park a ten minute car ride away. Close to goose island brewery,

Nov. 28 – Dec. 5

$237 CAD per night

Guest favourite

Condo in Chicago

4.98 out of 5 average rating, 233 reviews

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!

Sep. 12 – 19

$356 CAD per night

Superhost

Condo in Chicago

4.87 out of 5 average rating, 107 reviews

Spacious Duplex in Great Location

This below-grade unit has everything you want! Nestled on a quiet tree-lined street public transport is close by and downtown is a quick car ride away. The condo has lots of space and all the amenities you can ask for - plenty of parking, a King sized bed with premium linens, a luxury memory foam mattress, walk-in closet to store all your things, double spa shower, and a coffee bar stocked with top shelf Nespresso coffee. This unit books up quickly, so grab it today!

Sep. 18 – 25

$161 CAD per night

Guest favourite

Condo in Chicago

4.91 out of 5 average rating, 233 reviews

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.

Apr. 27 – May 4

$300 CAD per night

Guest favourite

Condo in Oak Park

4.88 out of 5 average rating, 164 reviews

Attractive Flat - Historic Oak Park

Attractive One Bedroom Flat for Rent in Historic Downtown Oak Park. Truly - one of the Best Locations in all of Chicago. Two Blocks from the Epicenter of this lovely city. Easy Access to Public Transportation to Downtown Chicago or the Greater Metro Area. The Elevated train -and- the Metra Train (15 Minutes by Train to Downtown) are each a quick walk. See “ property description “ For Important information for all perspective Guests:

Oct. 21 – 28

$217 CAD per night

Guest favourite

Condo in Chicago

4.86 out of 5 average rating, 123 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.

Jan. 13 – 20

$171 CAD per night

Guest favourite

Condo in Oak Park

4.98 out of 5 average rating, 126 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.

Sep. 9 – 16

$341 CAD per night