Condo vacation rentals in West Side

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Top-rated condo rentals in West Side

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Guest favorite

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 31 – Feb 7

R2,304 ZAR per night

Guest favorite

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!

Oct 25 – Nov 1

R2,930 ZAR per night

Superhost

Condo in Chicago

4.86 out of 5 average rating, 191 reviews

Bold Ukrainian Village 2 Bedroom w/Garage Parking

Our bright Ukrainian Village apartment is on a quiet, tree-lined street, but near some of the most exciting restaurants, bars, and vintage shops in the city, and only a mile north of the United Center - it's the best of all worlds! The layout is equally ideal for friends traveling together as it is families, as well as work from home life. We've got a backyard and patio for you to share, we're walking distance to Wicker Park, and close to plenty of CTA options that'll get you down to the Loop.

Nov 17 – 24

R3,672 ZAR per night

Guest favorite

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

R2,936 ZAR per night

Superhost

Condo in Chicago

4.86 out of 5 average rating, 437 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!

Jun 20 – 27

R3,232 ZAR per night

Guest favorite

Condo in Little Italy

4.96 out of 5 average rating, 120 reviews

Private hot tub - King bed suite - Free parking

Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

Jun 14 – 21

R5,449 ZAR 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,

Apr 17 – 24

R2,544 ZAR per night

Guest favorite

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 1 – 8

R3,922 ZAR 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!

Aug 11 – 18

R2,496 ZAR 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 17 – 24

R3,180 ZAR per night

Guest favorite

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:

Jul 18 – 25

R2,562 ZAR per night

Guest favorite

Condo in Chicago

4.86 out of 5 average rating, 124 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.

Dec 3 – 10

R2,087 ZAR per night