Holiday houses in South Loop, Chicago

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Top-rated holiday rentals in South Loop, Chicago

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Guest favourite

Home in Pilsen Historic District

4.95 out of 5 average rating, 367 reviews

Get Cozy at a Powder-Blue Residence in the Heart of Pilsen

House is perfectly located within walking distance of Pilsen's best attractions. Home is furnished and newly renovated with the idea of making your stay as comfortable as possible. Walking distance from Thalia Hall and many other great restaurants and coffee shops. For your convenience there is a "corner store" steps from the home where you can purchase food and beverage items. The whole apartment is professionally cleaned after every guest no matter how many days they have stayed. Fresh sheets and towels are provided for all guests as well. Walking distance from local favorites: Simone’s, Honky Tonk BBQ, Dusek's/Punch House/Thalia Hall, 5 Rabanitos, Furious Spoon, S.K.Y and HaiSous. Located 2 miles South West of Downtown Chicago. Extremely close to South Loop and West Loop. Amenities: - Washer and Dryer (located in unit) - Granite counter tops - All new appliances - Tiled bathroom - Central Heat/AC - Private back deck - Closet space All access, full kitchen, washer and drier in apartment. Private entrance with Keyless entry. Available at any time, happy to answer any questions you may have. Interaction will be dictated by guests. This is a vibrant family neighborhood with character, art, great food, and culture. Walk to amazing restaurants, bars, and coffee shops, including local favorites Simone’s, Honky Tonk BBQ, 5 Rabanitos, Furious Spoon, S.K.Y, and HaiSous. Close to major Chicago highways: I-190: Kennedy Expressway I-290: Eisenhower Expressway I-55: Stevenson Expressway I-90/94: Chicago Skyway, Dan Ryan Expressway, Kennedy Expressway, Jane Addams Memorial Tollway Public transit easily accessible: CTA Bus #8, 18, 60 CTA Trains: Blue, Pink and Orange Lines Divvy Bike Rental Station one block away Permit Parking $6-10 dollar Uber to Downtown

Guest favourite

Rental unit in Lincoln Park

5 out of 5 average rating, 235 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.

Guest favourite

Rental unit in Chicago

4.91 out of 5 average rating, 102 reviews

Ground-Level Speakeasy: 1BR-1.5BA Near Everything!

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.

Guest favourite

Rental unit in The Loop

4.9 out of 5 average rating, 220 reviews

1BR South Loop Loft I SuperHost + Top Rated!

Modern & spacious 1-bedroom loft in Chicago's South Loop. Central location to Grant Park, Soldier Field, Museums, McCormick Place and more! With a walk & transit score of 97, enjoying Chicago's fantastic restaurants, bars, and shopping options is a breeze. Our loft gets incredible natural light, has luxuriously tall ceilings and plenty of room to accommodate your entire group. Guests are always pleasantly surprised by the size of the space, curated design and the modern amenities we provide.

Guest favourite

Home in West Loop

4.98 out of 5 average rating, 347 reviews

Cozy garden apartment historic Jackson Bvld.

Just a short walk to the United Center our cozy 1 bdrm garden apt is located on Historic Jackson Blvd's tree lined st. Stop back & warm up by the fireplace before heading out to near by shopping & restaurants. Less than an hour from Midway or O'Hare. Walking distance to Randolph St. Restaurant Row, Little Italy, Greek Town, Union Pk, Fulton Warehouse Dist, Rush Hospital and UIC. A quick train/bus to The Loop, Theater Dist, Mag Mile, Wicker Pk. Free, convenient street pkg.

Guest favourite

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 favourite

Rental unit in Chicago

4.98 out of 5 average rating, 180 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.

Superhost

Rental unit in Pilsen Historic District

4.82 out of 5 average rating, 465 reviews

Eclectic Artist Designed Sanctuary Heart of Pilsen

Start the day with a soothing cup of tea or Nespresso on the front stoop in the morning sunshine. White hardwood floors combine with mismatched artwork, glossy houseplants, and a classic leather Chesterfield for restorative afternoon naps. This apartment is owned and designed by an artist/musician and a philosopher. It is solely used for AirBnb guests, so it will truly feel like your own space. Come stay to get away, relax, and be inspired!

Guest favourite

Rental unit in Little Italy

4.98 out of 5 average rating, 222 reviews

Spacious 2BR on Quiet St - Free Park/Late Checkout

2 bedroom, 1 bathroom apartment, located just off Taylor Street in the heart Little Italy! Views of the Sears Tower from the front yard. Safe and lively neighborhood, packed with diverse restaurants, cafes, bakeries, parks, etc. all just a short walk from the apartment! Nearby West Loop also packed with trendy shops and amazing dining spots. Flat screen TV in every room, In-unit laundry, patio space, coffee/tea provided. 1pm check out!

Superhost

Rental unit in Pilsen Historic District

4.87 out of 5 average rating, 275 reviews

Modern

Welcome to Pilsen, the neighborhood I have been living for 20 years! It is really cool and artsy. Forbes Magazine named the Pilsen neighborhood as one of the 12 coolest neighborhoods in the world. https://www.nbcchicago.com/blogs/worth-the-trip/Chicago-Neighborhood-Named-Among-Coolest-in-World-by-Forbes-486702851.html https://chicago.suntimes.com/news/pilsen-chicago-forbes-coolest-neighborhoods/

Superhost

Guest suite in West Loop

4.88 out of 5 average rating, 107 reviews

Cozy one-bedroom suite in the heart of West Loop

Enjoy your trip to Chicago in the heart of Fulton Market in this cozy, one-bedroom guest suite. Whether you’re visiting friends or here for business, this guest suite is the perfect space to unwind at the end of the day. Grab dinner at Chicago’s top-rated restaurants in Fulton Market and West Loop, all within a 10 minute walk. Go out for the night at some of Chicago’s best bars and nightlife.

Guest favourite

Rental unit in Near South Side

4.96 out of 5 average rating, 144 reviews

Sprawling South Loop 3Br/2Ba with parking

Conveniently located near McCormick Place and Soldier Field. Close to parks, shopping, and public transportation. Newly remodeled unit. Second floor unit with no elevator in building. Modern bathrooms and kitchen, new fixtures throughout, nice front deck, in-unit full-sized washer and dryer, hardwood floors throughout. One parking space included, but absolutely NO OVERSIZED VEHICLES