Holiday houses in Grant Park

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Top-rated holiday rentals in Grant Park

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Top Guest favourite
A light-filled living area features a gray sectional sofa adorned with blue and yellow cushions. Two large windows provide perspectives of the outdoors. A world map hangs on the wall, complemented by a small coffee table and a patterned area rug, contributing to a cozy setting.
Apartment in Lincoln Park
5 out of 5 average rating, 286 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.

Top Guest favourite
A modern kitchen and living area are showcased within an open-concept space. The kitchen features stainless steel appliances and a large island with seating for three. The cozy living area includes comfortable seating and a low wooden coffee table, complemented by warm wooden flooring.
Apartment in Chicago
5 out of 5 average rating, 62 reviews

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.

The exterior of a modern high-rise building is visible, featuring large glass windows and a curved architectural design. Surrounding trees line the street, creating a blend of urban and natural elements. The image showcases the building's height against a clear blue sky.
Apartment in South Loop
4.8 out of 5 average rating, 327 reviews

Kasa | Studio, Walk to Grant Park | South Loop

It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking distance of the Museum Campus, McCormick Place Center, and a variety of restaurants and shops. Our Kasas are the best choice for your trip to the Windy City with our spacious floorplans, full kitchen, laundry facilities, and parking. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text, phone, or chat, and a Virtual Front Desk accessed via mobile device.

Top Guest favourite
Private room in South Loop
5 out of 5 average rating, 135 reviews

Urban Oasis Pilsen - guest room in townhouse

Experience the charm of Pilsen, one of Chicago's trendiest neighborhoods. Your private bedroom features a queen-size bed and an en-suite bathroom with a tub/shower. The room includes a small desk, ample storage space, and a TV with streaming services. Triple-paned windows provide plenty of natural light while minimizing noise from the nearby I-90/94 freeway. The room is located on the third floor (40 steps)! The second floor offers access to the kitchen, living room, TV den, and balcony.

Guest favourite
A vintage-style sign featuring bold red and white lettering, stating 'Bohemian Lodge no 17' against a dark brown background. Decorative elements include images of beer glasses and whimsical knot designs, creating a nostalgic atmosphere.
Apartment in Lower West Side
4.85 out of 5 average rating, 309 reviews

Teeny Tiny Bohemian Lodge - Clean & Affordable

Explore the wonderful neighborhood of Pilsen from this unique little space. Private entrance to your bedroom with an attached bathroom with shower. The entire space is for your private use- nothing is shared. NOTE the bedroom & bathroom ARE the entire space. Designed for one person as a sleeping room. We can not host 2 people. Twin size American bed is 38 x 75 inches. Please CLICK "show more " below BEFORE YOU BOOK/INQUIRE I need you to read and respond to our house rules.

Top Guest favourite
A modern living space features a light-colored sofa with decorative pillows and a woven throw. A warm-toned wooden accent wall complements a sleek electric fireplace below a mounted television. A patterned area rug anchors the room, while shelves in the background display decorative items.
Loft in South Side
4.99 out of 5 average rating, 126 reviews

Lovely Garden Studio in Chicago

Kick back and relax in this calm, stylish space. Located in historic Bronzeville, our modern studio boasts open-plan living, stylish finishes and plenty of room to accommodate up to 3 guests. Our garden studio is located walking distance to the Green Line station, a 10 minute drive to downtown loop, 15-20 minutes away from Midway Airport, 5 minutes to Lake Michigan, and 5 minutes away from McCormick Place Convention Center, IIT, and Hyde Park/University of Chicago.

Guest favourite
The image showcases a well-lit studio featuring a cozy sleeping area with a spacious bed adorned in striped linens. A small table and chairs are placed near a window, allowing natural light to fill the room. The lower section depicts a shared rooftop deck with outdoor seating, vibrant planters, and a grill, offering city views.
Condo in Grant Park
4.93 out of 5 average rating, 59 reviews

Mich Ave Downtown Penthouse - Rooftop+Gym

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 -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 favourite
A private room features a spacious bed with crisp white bedding. A wall-mounted television is situated opposite, with a small table and chair nearby. A fan is positioned to the side, and a compact refrigerator is visible next to the table. Natural light filters through sheer curtains.
Private room in Hyde Park
4.92 out of 5 average rating, 285 reviews

HydePark002, UC, NavyPier, Chinatown, freeparking

Feel free to check us other listings: https://www.airbnb.com/h/hydepark001 https://www.airbnb.com/h/zengarden333 https://www.airbnb.com/h/zengarden332 https://www.airbnb.com/h/zengarden001 Hyde Park luxury private room with a keypad lock on each room door. Shared full bathroom only for 2 rooms. Step to UChicago, Chicago loop, McCormick, Chinatown(hundreds of delicious food). Perfect for everyone in Chicago! Free street parking.

Guest favourite
The modern kitchen features white cabinets and a polished countertop. Stainless steel appliances, including a gas stove and dishwasher, are visible. A window allows natural light to enter, illuminating the functional space.
Guesthouse in West Town
4.95 out of 5 average rating, 41 reviews

Cozy Coach House Retreat Near Downtown!

Fully remodeled coach house centrally located in Chicago! Most tourist attractions are within a 15 drive or less! Public transportation is within a 3 min walk. You'll also have access to the shared rooftop deck (Furniture available May 5th-Sept 30th). This cozy unit offers 1 Queen bed + 1 bath, 1 Queen size air mattress provided, fully stocked kitchen and spacious living room space! Free Street Parking in the Area

Top Guest favourite
Private room in West Rogers Park
4.99 out of 5 average rating, 168 reviews

At the junction of comfort and care

Your warmly-decorated guest room has a queen-size memory foam mattress for a good night’s sleep. A meticulously kept bathroom is adjacent to your room. Parking is free and easy. Downtown is 17 minutes by car along Chicago's lakefront and 50 minutes by public transit. Little India in our West Ridge neighborhood is a noteworthy dining destination. Enjoy basing your Chicago stay here!

Top Guest favourite
A spacious living room features three large windows allowing natural light to fill the space. Comfortable seating includes a leather couch and an armchair. A television is mounted on the wall, and a decorative area rug lies beneath a wooden table set for dining.
Condo in Noble Square
4.97 out of 5 average rating, 840 reviews

Great location. Free parking.

Great location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, cable TV, dvd/Blu-ray, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.

Superhost
A modern bedroom features a plush, spacious bed with a tufted teal headboard. Decorative pillows add a subtle pop of color, while a sleek bedside lamp sits on a wooden nightstand. Neutral walls enhance the serene ambiance of the room.
Hotel room in Grant Park
4.78 out of 5 average rating, 405 reviews

A polished, modern affair on iconic Michigan Ave.

Experience an upgraded stay at Le Méridien Essex Chicago, located on Michigan Ave in the city's heart. Our luxury hotel, surrounded by iconic attractions, offers modern rooms with stunning views of Grant Park, Lake Michigan, Buckingham Fountain, and the Museum Campus. We're committed to making your stay in the Loop unforgettable.

Popular amenities for Grant Park holiday rentals

Quick stats about holiday rentals in Grant Park

  • Total rentals

    100 properties

  • Nightly prices starting at

    $62 AUD before taxes and fees

  • Total number of reviews

    4.6K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    60 properties allow pets

  • Rentals with a pool

    50 properties have a pool

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