Condo vacation rentals in Chicago

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Top-rated condo rentals in Chicago

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Guest favorite

Condo in Chicago

4.84 out of 5 average rating, 303 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.

Apr 6 – 13

ﺩ.ﺇ537 per night

Guest favorite

Condo in Chicago

4.91 out of 5 average rating, 120 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.

Mar 8 – 15

ﺩ.ﺇ659 per night

Guest favorite

Condo in Chicago

4.93 out of 5 average rating, 186 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.

Apr 9 – 16

ﺩ.ﺇ365 per night

Guest favorite

Condo in Chicago

4.88 out of 5 average rating, 234 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 8 – 15

ﺩ.ﺇ583 per night

Superhost

Condo in Chicago

4.86 out of 5 average rating, 435 reviews

Humboldt Park Traveler's Lodge

Come stay at my gorgeous condo! Featuring exposed brick, a private entrance, stainless steel appliances, and a queen bed -> all on a quiet tree lined street! It's a perfect place to re-energize between big city adventures. Free street parking, and a 5 min walk to some of the best independently owned shops, restaurants, and bars in the city. Also, the massive and incredible Humboldt Park is also just a 5 min walk away! Please reach out for recommendations - I love giving them to people!

May 20 – 27

ﺩ.ﺇ538 per night

Guest favorite

Condo in Chicago

4.92 out of 5 average rating, 110 reviews

Stunning, Spacious, & Sun-Soaked 1br Uptown Condo

Perfect for any type of traveler, my bright and inviting one bedroom condo in Uptown is a sanctuary stocked with every amenity you could need! There's an organized workspace area if you bring your work with you to Chicago, a gorgeous sunroom with a sofa bed, and a beautiful kitchen stocked with everything you could need to whip up a delicious meal. Steps to the lakefront and Montrose Beach and just a 6-minute walk to the Wilson Red Line, you can't beat this location. Book today! Welcome!

Jan 10 – 17

ﺩ.ﺇ552 per night

Guest favorite

Condo in East Garfield Park

4.9 out of 5 average rating, 135 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,

Jan 4 – 11

ﺩ.ﺇ505 per night

Guest favorite

Condo in Chicago

4.98 out of 5 average rating, 232 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!

Jan 4 – 11

ﺩ.ﺇ689 per night

Superhost

Condo in West Town

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!

Aug 16 – 23

ﺩ.ﺇ490 per night

Guest favorite

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.

Nov 13 – 20

ﺩ.ﺇ631 per night

Guest favorite

Condo in Oak Park

4.88 out of 5 average rating, 163 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:

May 2 – 9

ﺩ.ﺇ465 per night

Guest favorite

Condo in Chicago

4.99 out of 5 average rating, 561 reviews

Urban Comfort in the Heart of Chicago

Proud to be amongst the highest rated listings in the city. This is the PRIVATE first floor of our duplex condo, with your own entrance/exit, 75" flatscreen TV, central heat/air, and an en-suite bathroom. We are in the middle of Chicago's vibrant Northside while still having the benefit of coming home to a tree lined one lane residential street. Please contact us with any questions at all before you book your stay.

Jul 24 – 31

ﺩ.ﺇ817 per night