Condo vacation rentals in Chicago Loop

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Top-rated condo rentals in Chicago Loop

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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 East Rogers Park

4.91 out of 5 average rating, 128 reviews

Magnificent Place & A Parking Space

1 Bedroom with 1 bathroom This spacious, quiet condominium is located in the Rogers Park neighborhood of Chicago, 3 minute walk from the local pubs, restaurants, shopping, and tennis court. Great for weekend trips as the beach is a quick bike ride 5 minute bike ride. Metra UP-Northwest, a 17 minute train ride to Downtown Chicago (4 min walk West to catch this train). CTA Morse Red Line Train is also available, making multiple stops on its way Downtown (5 min walk East to catch this train).

Superhost

Condo in Gold Coast

4.88 out of 5 average rating, 179 reviews

2BD/2BA MAG MILE MASTERPIECE (+Rooftop)

Welcome! Guests love our home because: - You're SECONDS from the LAKE and MAGNIFICENT MILE - You're steps away from the famous Drake Hotel and Oak Street Beach. - Walk to every popular attraction that makes Chicago so great! - Newly remodeled interior with an open floor plan layout - Tranquil rooftop overlooking the Lake - Fast WIFI - Super comfy beds! - Custom chef kitchen - Located on a quiet street - Lake Michigan view from our floor-to-ceiling windows We look forward to hosting you!

Guest favorite

Condo in Little Italy

4.96 out of 5 average rating, 159 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.

Guest favorite

Condo in Wicker Park

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 West Town

4.96 out of 5 average rating, 107 reviews

Downtown Chicago - Spa Bath, Patio, 3 blocks to L

Explore Chicago's charm just moments from downtown! This Airbnb boasts a spa bath with a luxurious rain shower and jetted tub, a fully equipped kitchen for culinary adventures, comfortable reclining sofas for relaxation, and ample space to unwind. Sleep like royalty in the master bedroom's king bed, and a queen murphy bed in the living area ensures a comfortable stay for up to four guests. Step outside to the patio with a fire pit for cozy evenings. Your Windy City getaway begins here!

Superhost

Condo in West Town

4.78 out of 5 average rating, 131 reviews

Cabin 306 at 747 Lofts

This studio apartment is in the perfect location in Chicago for getting to Downtown via the Blue Line L or to the Hot West Loop and Randolph street restaurant row. Walk to bars, shops, restaurants, coffee liquor stores and transportation with ease! You will love our spa baths, in unit laundry and full modern kitchens to make it feel like a home away from home. One of the best pizza spots in Chicago is only steps away! Early Check-Ins and Late Check-Outs are difficult to accommodate.

Guest favorite

Condo in The Loop

4.88 out of 5 average rating, 105 reviews

Downtown Park #11 - Mich Ave PH | gym+rooftop

Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Guests love staying with us because: -Central Location on Grant Park (no car needed!) -FAST WIFI -En-suite Laundry -Did we mention the Lake & Park are outside our front door? -Comfy Queen bed -Loft style bedroom -Shared Rooftop Deck stunning views -Gym -3 blocks from Red "L" subway -Close to Grant Park, The Bean, Soldier Field, Museums If you are looking for a special place, you've found it!

Guest favorite

Condo in Lincoln Park

4.92 out of 5 average rating, 273 reviews

Old Town Pied-à-Terre w/Pvt Terrace and Parking

Our bright modern 2 bedroom condo has 13 ft ceilings and an amazing private terrace. It's in the heart of Old Town, right on Wells St - steps outside the door are some of the city's best restaurants, cafes, and bars. Just a 5 minute walk to two world-renowned comedy clubs: Second City and Zanies. The Chicago History Museum, Lincoln Park Zoo, and the lake are a quick walk too. The Sedgwick CTA stop is nearby too! Please note: patio cushions are available May through October.

Guest favorite

Condo in West Loop

4.95 out of 5 average rating, 210 reviews

Updated Designer Duplex In Fulton Market W/parking

We completed our luxury renovation in kitchen, bathrooms, and patio with a fire pit! We hope you enjoy! The first thing you notice stepping into my house are the sky-high ceilings! Enormous floor to ceiling windows allow light to stream into the the 2 floor home. The stylish and very large terrace are great for summer nights. Walk out the front door & you are in the heart of restaurant row with all the best bars and restaurant in the city. Parking included!

Guest favorite

Condo in River North

4.98 out of 5 average rating, 128 reviews

City Center Oasis: 3BR/2BA✔︎ Patio✔︎ Parking(2x) ✔︎

Perfectly in the heart of Chicago in the River North neighborhood. You will experience Chicago easily from here! • Free parking (2) in our attached lot! • Surrounded by world class shopping on the Magnificent Mile • In the heart of the city's best dining and walking to big-city nightlife • Walk to Lake Michigan and Navy Pier • Steps from the local trains and buses to reach the outer parts of the city