Holiday rentals in Grant Park

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Grant Park

Guests agree: these stays are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1
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.
Flat in Lincoln Park
5 out of 5 average rating, 288 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.
Flat in Chicago
5 out of 5 average rating, 69 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.

Guest favourite
An indoor swimming pool is shown, featuring clear blue water and black lane markers. Lounge chairs are arranged along the sides, and large windows allow natural light to fill the space, enhancing the modern design with sleek lines and minimalistic decor.
Flat in South Loop
4.96 out of 5 average rating, 68 reviews

The Downtown Oasis (2BD / 2BA)

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 favourite
A modern lounge area is highlighted by large floor-to-ceiling windows, offering expansive views of the Chicago skyline. Two round, cozy chairs are positioned near a small round table, complemented by a plush sofa. Green plants add a touch of nature to the space.
Flat in Printer's Row
5 out of 5 average rating, 24 reviews

14th Floor 3Bd 3Bth Unit w/ Gym, Pool, &Amenities

Welcome to your spacious urban getaway in the heart of Chicago’s Printer’s Row neighborhood! This modern 3-bedroom, 3-bathroom unit is located in a stunning high-rise building, offering sweeping city views and access to premium amenities—perfect for families, business travelers, or groups looking to explore the best of downtown. Whether you're here for work or play, this retreat offers the perfect blend of style, comfort, and location. Book your stay today and experience Chicago like a local!

Top guest favourite
A contemporary loft bedroom features a spacious bed with a light grey quilt. Exposed brick walls complement framed vintage Chicago artwork. Soft lighting is provided by string lights near the window. A green plant adds a touch of nature, while dark wood accents create warmth.
Loft in Lake View
4.96 out of 5 average rating, 543 reviews

Lakeview Loft-Vintage Chicago, Modern Amenities

The Lakeview Loft is a freshly remodeled loft space with a vintage Chicago theme and modern amenities. Located in the Lakeview neighborhood, it is 1/2 mile to the Brown & Red Line el trains, less than a mile to Wrigley Field and 1.5 miles to the lakefront. The Lakeview Loft will provide guests a true Chicago experience while staying in a great Chicago neighborhood. We believe in giving back to our neighborhood as well so for each booking we donate $5 to a local children's charity.

Superhost
A modern living space is presented, featuring a comfortable dark couch adorned with textured throw pillows. A sleek arc floor lamp provides soft lighting, and a small dining table by the window offers a view of Lake Michigan. A framed artwork adds a splash of color.
Flat in Grant Park
4.85 out of 5 average rating, 110 reviews

Downtown Mich Ave #10 | 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 Double 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!

Superhost
A serene indoor pool area is highlighted by tall glass walls, allowing natural light to illuminate the space. Cozy seating with soft cushions is arranged around the pool, while overhead greenery and pendant lights create a calming atmosphere.
Flat in Grant Park
4.72 out of 5 average rating, 172 reviews

Sentral Studio Apt in South Loop Chicago

Indoor/Outdoor Resort-Style Pool • Grilling Station • Four-Story Indoor Garden • Fitness Center • Demonstration Kitchen • Pet Friendly w/ Amenities • Co-Working Space w/ High-Speed WiFi • Across from Grant Park • Steps to South Loop Dining & Nightlife • Breathtaking Views of Lake Michigan & the City Skyline Sentral Michigan Ave offers upscale comfort in the heart of Chicago’s South Loop, blending premium amenities with unmatched access to parks, culture, and entertainment.

Superhost
Flat in West Loop
4.9 out of 5 average rating, 41 reviews

Downtown Luxury|Cozy Stay| Walk to Millennium Park

Elevator access, 45th floor with an amazing view Smart TV, fast Wi-Fi, work-friendly space Washer/dryer in the building Stay warm and connected in the heart of Chicago’s Loop. Just steps from the Christkindlmarket, Millennium Park, and top restaurants. Perfect for travelers and families exploring the city this winter. This Bright /Airy unit has 1 California king bed, 1 large sofa that could be use as another bed and 1 airbed so you can stay with your family or friends!

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, 128 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
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.
Flat in South Loop
4.89 out of 5 average rating, 261 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 favourite
A rooftop pool area is showcased, featuring clean lines and modern architecture. The pool is rectangular and bordered by sleek railings. Surrounding urban buildings are visible against a clear blue sky, highlighting the vibrant city atmosphere.
Flat in Printer's Row
4.82 out of 5 average rating, 34 reviews

South Loop | Rooftop With In & Out Parking | 2

Enjoy a stylish experience at this centrally located place! This stunning 1,000 sq. ft. modern 2-bedroom, 2-bathroom unit is perfect for corporate travelers and families looking for a chic escape in downtown Chicago 🏡 🔥 Rooftop Patio W/ BBQ 🏊 Rooftop Pool 🚗 Free In/Out Parking (5-Min Walk to Garage) 🛏️ 2 Bedrooms | 2 Bathrooms 🛌 2 Queen Beds 🛌1 Inflatable Airbed 👶 Portable Crib (For Mini Travel Companion) 🎬 Netflix, Hulu, Disney+ & Prime Included

Guest favourite
A bright living area features a deep green accent wall and polished concrete floors. A plush dark sofa with decorative pillows is positioned facing a television on a wooden stand. A window offers a view of an outdoor space, enhancing the natural light in the room.
Flat in Chicago Loop
4.93 out of 5 average rating, 87 reviews

Loop Loft-Subway & Art Institute

Urban Elegance Meets Prime Location! Welcome to our chic hard loft in the heart of the Chicago Loop. Experience city living at its finest, where industrial charm marries modern luxury. Features: - Authentic loft with polished concrete floors - Soaring high ceilings - Elegantly furnished Location: - Right in Chicago's vibrant Loop district - Walk to Millennium Park, Art Institute of Chicago, Mag Mile, Riverwalk, and more

Popular amenities for Grant Park holiday rentals

When is the best time to visit Grant Park?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$155 SGD$164 SGD$220 SGD$277 SGD$334 SGD$363 SGD$400 SGD$375 SGD$336 SGD$307 SGD$231 SGD$201 SGD
Avg. temp-3°C-1°C4°C10°C16°C22°C25°C24°C20°C13°C6°C0°C

Quick stats about holiday rentals in Grant Park

  • Total holiday rentals

    Explore 100 holiday rentals in Grant Park

  • Nightly prices starting at

    Grant Park holiday rentals start at $52 SGD per night before taxes and fees

  • Verified guest reviews

    Over 4,640 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 60 rentals that welcome pets

  • Holiday rentals with a pool

    50 properties feature pools

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    90 of Grant Park holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Grant Park rentals

  • 4.7 Average rating

    Grant Park stays receive an average rating of 4.7 out of 5 from guests

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago
  6. Grant Park