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

4.9 out of 5 average rating, 100 reviews

Unique 2BR/2BA FREE Parking/WI-FI Minutes From DT

Traveling to Chicago and looking for the PERFECT place to stay? This Cozy unit is PERFECT for Business trips, Romantic Getaways or just relaxing with family. Its located in the Pilsen area, ChinaTown area just minutes from Downtown and the McCormick Place, United Center, Rush Hospital, West Loop,South Loop, Michigan Ave, White Sox Stadium. This listing offers FREE street parking on both sides of the street and Not to mention, it’s near plenty of shopping, Dining and Fun. Can't wait to host you!

Guest favorite

Condo in Chicago

4.86 out of 5 average rating, 347 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.

Guest favorite

Condo in Chicago

4.89 out of 5 average rating, 257 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!

Superhost

Condo in Chicago

4.85 out of 5 average rating, 126 reviews

Tri-Taylor/Medical Dist. near West Loop

Enjoy this stylish Newly Rehabbed condo equipped with 3 bedrooms and 2 bathrooms. Modern kitchen with stainless steel appliances. ~UNITED CENTER home of the Chicago Bulls and Blackhawks located within 2-3 min walk *2 blocks*. 4-7 min drive to little Italy restaurants/Tri Taylor/Medical District. Near Downtown (5-7min drive). 2 Blocks from the blue line ~Free street parking ~Washer Dryer ~Dishwasher ~spacious Back patio Parties are restricted due to COVID guidelines for the city of Chicago.

Guest favorite

Condo in Chicago

4.96 out of 5 average rating, 143 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.

Guest favorite

Condo in Chicago

4.94 out of 5 average rating, 131 reviews

CHIC DOWNTOWN PENTHOUSE w/ private roof +parking

Escape into this prime, Chicago Penthouse! Guests love this home because: - Surrounded by top-notch restaurants/retail - Close to all popular attractions that make Chicago so great - Luxurious, newly-renovated interior filled with natural light - Open-floor plan for entertaining! - Private, spacious roof deck viewing the entire Chicago skyline! - Fast WiFi (600 mbps) - Master en-suite w/ separate walk-out - Designated parking spot! - Steps away from blue line Damen station (800 feet)

Guest favorite

Condo in Chicago

4.91 out of 5 average rating, 159 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,

Superhost

Condo in Chicago

4.87 out of 5 average rating, 126 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!

Guest favorite

Condo in Chicago

4.93 out of 5 average rating, 110 reviews

Modern Chicago Movie Themed Apt

Welcome to Chicago at the Movies! An amazing fully updated apartment in the Ukrainian Village neighborhood. This midcentury modern 3 bedroom home is perfect for groups, couples, and families looking for a perfect Chicago vacation. The property is conveniently located on Grand Avenue just minutes by car, bus or train from Downtown and the Lakefront. We are also just a short 5 Minute ride to the United Center for concerts sports and more!

Superhost

Condo in Chicago

4.86 out of 5 average rating, 164 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.

Guest favorite

Condo in Oak Park

4.95 out of 5 average rating, 185 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.

Guest favorite

Condo in Chicago

4.98 out of 5 average rating, 325 reviews

Sunny Apartment Just 2 Blocks from Wrigley and Boystown

Located on a quiet, tree-lined street, the apartment sits on the second storey of a classic Chicago house in Lakeview—a vibrant lakefront community with arts and culture, green space, eateries, boutiques, nightlife, and transportation options. Street parking passes available upon request. Less than five minute walk to red line El (subway train) stop and several bus lines.