Apartment vacation rentals in Grant Park, Chicago

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Top-rated apartment rentals in Grant Park, Chicago

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Top guest favorite

Apartment in Lincoln Park

5 out of 5 average rating, 263 reviews

Explore Lincoln Park from a Polished Apartment

This apartment is a large studio in the heart of Lincoln Park! New construction and all furnishings & appliances are brand new. It is perfect for a couple...but can also sleep 3-4 for a girls trip or a family with small children. You enter with your personal keypad code which we give you a few days prior to your stay. And we are always available by text or email should you have any questions about the apartment. Set in Lincoln Park, this apartment is steps away from shopping along Armitage and Halsted Avenue. There’s grocery stores, restaurants, and cafes nearby, plus red and brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment and we offer free residential parking stickers in the apartment on the desk. We also offer a clean garage space (with free EV hook up, should you need it) for $20/night.

Superhost

An indoor swimming pool is featured, flanked by ample natural light from large windows. Comfortable seating is arranged alongside the pool, complemented by potted plants and a calming color palette. Distinctive tile work adorns the floor, adding texture to the serene atmosphere.

Apartment in South Loop

5 out of 5 average rating, 4 reviews

The South Loop Suite

Located at the epicenter of Chicago's cultural, historical, and business attractions, this luxurious 2 bedroom apartment offers guests all the comforts of home, whether on the road for work or play. Within walking distance are world famous attractions including: Millennium Park, The Bean, Navy Pier, Riverwalk, Soldier Field, The Field Museum, and more. Additionally, guests are merely a couple blocks from an "L" train stop, which will transport passengers anywhere they could desire in the city.

Guest favorite

A vibrant living area showcases eclectic décor, featuring a colorful mural with artistic motifs on one wall. A round coffee table sits in the center, surrounded by cream-colored sofas adorned with green cushions. A wet bar with wooden stools is visible in the background.

Apartment in South Side

4.92 out of 5 average rating, 121 reviews

Hidden Gem:Artsy Speakeasy in Historic Bronzeville

Enjoy this fun and unique 1-bed 1.5-bath speakeasy in the heart of Chicago's Bronzeville District. This artsy vibe features eclectic décor, hand-painted murals, Smart TVs, wet bar, wellness studio, remote workspace, free street parking, and ground-level-step-free access. This cozy space is perfect for fun couples, solo adventurers, business travelers, and game night aficionados. Easy access to Downtown (6 miles to Mag Mile, Navy Pier, Millennium Park), Beach (1 mile), Museums, & Sports arenas.

Top guest favorite

The bedroom is designed with a spacious bed centered against an accent wall featuring geometric patterns. A plush bench is positioned at the foot of the bed. Warm lighting illuminates the room, complemented by rich curtains and wooden flooring.

Apartment in Magnificent Mile

4.98 out of 5 average rating, 158 reviews

Elegant Suite in Gold Coast

Established in 1927 as the first headquarters for Elizabeth Arden in Chicago, the Walton Residence is located in the heart of the Gold Coast neighborhood of Chicago. Steps away from the Magnificent Mile, and the high-end boutiques of Oak and Rush Street, we are perfectly situated in the middle of the action for your Chicago adventure. ***From Sept. to beginning of Dec. 2024, there will be repairs to the exterior of the building. We do not expect this to cause major interruptions to your stay.

Guest favorite

An open living space is divided into areas for relaxation and sleeping. A large bed with soft linens is showcased next to a contemporary TV stand. A sectional sofa is positioned to create a cozy sitting area, complementing the natural light filtering through the curtains.

Apartment in Pilsen

4.75 out of 5 average rating, 327 reviews

Bright & Spacious| Free Parking |Trendy Bridgeport

Step inside and be greeted by an open-concept space bathed in natural light. High ceilings, hardwood floors perfectly blend vintage charm with modern elegance. The living area invites you to unwind after a day of exploring our vibrant city. Relax on the sofa, watch your favorite shows on our large flat-screen TV, or indulge in book in the cozy seating nook. Whether you're a solo traveler, couple, or friend group looking for an unforgettable adventure, this is the ultimate urban retreat.

Superhost

A cozy sleeping area is presented with a spacious bed dressed in dark bedding, accented by two patterned pillows and a green decorative pillow. A soft teal blanket and folded towels are placed at the foot of the bed, while a framed artwork hangs on the wall above.

Apartment in Pilsen

4.82 out of 5 average rating, 22 reviews

Garden Apartment in Historic Pilsen Arts Area

This private garden unit is ideally located and well-equipped with everything you need for a comfortable homebase on your Chicago adventure. Come to Pilsen and experience one of Chicago’s most vibrant neighborhoods. With dozens of unique shops to explore, delightful coffee shops, Pilsen is a beating heart of arts and culture. Peruse charming streets filled with distinctive and historic architecture, admire beautiful street murals, and try one of Pilsen's many delicious taquerias.

Superhost

The entry to the studio features a full-size bed adorned with white bedding. Natural light enters through large windows, illuminating the space. A television is mounted on the wall opposite the bed, and a door leads to an outdoor area, framed by a charming entryway.

Apartment in Logan Square

4.77 out of 5 average rating, 368 reviews

Private Logan Square Studio

A private second floor walk up vintage studio apartment right in the heart of Logan Square. Located just half a block north of the picturesque Logan Boulevard and three blocks (5-8 minute walk) from the Logan Square blue line stop which is great for getting around the city. Logan Square is a 15 minute train ride into the loop and 20 minutes out to O'Hare. This studio is convenient for the weary O'Hare traveler or perfect for a private getaway from the hustle of Chicago.

Guest favorite

A spacious common area features large windows that allow plenty of natural light to fill the room. A modern entertainment unit is placed against a white brick wall, complemented by a comfortable sectional sofa and a round coffee table on a textured rug.

Apartment in South Loop

4.93 out of 5 average rating, 184 reviews

Lavish 2BR/2BA Loft I Next to Grant Park & Museums

Enjoy Chicago in our modern & spacious 2-bedroom loft in the South Loop. Central location to Grant Park, Soldier Field, Museum Campus, McCormick Place and more! Our location has a walk & transit score of 97, providing easy access to all the hot spots on your itinerary! Expect lovely natural light, luxuriously tall ceilings and room to accommodate your entire group. Guests are always pleasantly surprised by the size of the space and the modern amenities we provide!

Guest favorite

A spacious living area is highlighted by large windows that provide ample natural light. A contemporary sofa faces a round black table, complemented by a vibrant red area rug. A striking mural adorns the wall behind the seating, adding a bold artistic touch to the space.

Apartment in South Loop

4.88 out of 5 average rating, 243 reviews

1BR South Loop Loft I SuperHost + Top Rated!

Enjoy Chicago in our modern & spacious 1-bedroom loft in the South Loop. Central location to Grant Park, Soldier Field, Museum Campus, McCormick Place and more! Our location has a walk & transit score of 97, providing easy access to all the hot spots on your itinerary! Expect lovely natural light, luxuriously tall ceilings and room to accommodate your entire group. Guests are always pleasantly surprised by the size of the space and the modern amenities we provide!

Guest favorite

A modern kitchen features sleek black cabinetry and appliances, complemented by a contrasting white countertop. Stylish stools are arranged around a small kitchen island. The wall is adorned with a framed painting, while decorative items are displayed on open shelves above the countertop.

Apartment in Pilsen

4.87 out of 5 average rating, 264 reviews

Spectacular Pilsen Studio for 2!

This chic studio in the heart of Pilsen is the perfect space to kick back and relax during your visit to the Windy City! The vibrant neighborhood always has something to offer to any type of traveler, and it's a quick trip to see most of the iconic Chicago sights. Easily walk to historic Thalia Hall, or drive to the Loop in just 5 minutes! You'll love the thoughtful touches and modern decor in the apartment, as well as the bright and welcoming main space.

Top guest favorite

A green sofa is positioned in a bright living area, accompanied by a round coffee table. A decorative bowl and a potted plant sit atop the table, while a piece of wall art featuring a tree landscape adds character. Natural light enters through nearby windows.

Apartment in Chicago

4.99 out of 5 average rating, 230 reviews

Modern Apt with style & comfort in Pilsen Chicago

Enjoy a nicely updated studio in a safe, family-owned building located in Pilsen/Heart of Chicago conveniently located near Downtown, Chinatown, & Hyde Park to name a few. Public transportation is walking distance or you can go on a short drive to museums, parks, cafes, restaurants, bars, venues, and hip neighborhoods. Chicago has a full line up of festivals happening this year so feel confident in choosing my lovely space to be part of your experience.

Top guest favorite

A well-lit bedroom features a spacious bed with a patterned duvet and decorative pillows. A small dining table with two chairs is positioned near the kitchenette, which includes a stove and refrigerator. Large windows allow natural light to fill the room, complemented by soft curtains.

Apartment in Ukrainian Village

4.9 out of 5 average rating, 527 reviews

iKlektik House Chicago / Robin

CLOSE TO THE UNITED CENTER! Bright, Sunny and Stylish one bedroom, full kitchen, balcony overlooking the backyard in West Town WITH FREE STREET PARKING. Close to Wicker Park, Ukrainian Village West Town and Bucktown. The space is amazing...just read the reviews! Very cozy! There is FREE street parking. WiFi Speed has been upgraded to 1200mps!! NEW mini-split system that is very quiet heating and cooling. WE DO NOT RENT ON "CL" DO NOT WIRE $ IT'S A SCAM