The widest selection of unusual accommodations in Chicago, IL

A cabin, a lighthouse, a glamping, your extraordinary stay awaits you

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Chicago, IL unique stays
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74 Unique places to stay in Chicago, IL

Best family friendly Chicago, IL unique stays

Among the 74 accommodations in Chicago, IL, here are the 2 best family friendly unique accommodations

Tiny Cozy Guesthouse In Quiet Family Neighborhood - Chicago, IL
9.9 29 reviews

Tiny Cozy Guesthouse In Quiet Family Neighborhood

cabin, Dunning
This Chicago cabin rental, conveniently located in [Insert Specific Chicago Neighbourhood/Area – e.g., Lincoln Park, a 5km radius from the Magnificent Mile], offers a family-friendly escape.
Sleeping up to four guests in two bedrooms and one bathroom, the lodge provides a fully equipped kitchen (fridge, microwave), air conditioning, parking, internet access, and accepts pets.
Chicago Bungalow Near Wrigley Field W/ King Suite - Chicago, IL
9.6 269 reviews

Chicago Bungalow Near Wrigley Field W/ King Suite

bungalow, Chicago
This Chicago bungalow is situated just a short distance from Wrigley Field, in a safe and friendly neighbourhood with plenty of pubs and restaurants nearby. The property has received excellent ratings for its location, cleanliness and overall experience.
The three-bedroom house comfortably sleeps up to nine guests and offers a fully equipped kitchen, a private garden with access until 9pm, and super-fast internet. You’ll also find a separate entrance, a smart lock for easy access, and air conditioning for your comfort.

Best Chicago, IL unique stays with a pool

Jeffjack Heated Pool Penthouse In Chicago's West Loop - Chicago, IL
9.6 147 reviews

Jeffjack Heated Pool Penthouse In Chicago's West Loop

apartment, Chicago
This penthouse apartment is conveniently located in the centre of Chicago, within easy walking distance of Union Station, Willis Tower, and CIBC Theatre. The apartment consistently receives excellent ratings for its location, cleanliness, and overall experience, making it a popular choice for travellers.
The apartment has two bedrooms, comfortably accommodating up to six guests. Enjoy a range of amenities including a rooftop pool, fitness centre, and private parking, as well as a fully equipped kitchen and balcony with stunning city views.

Frequently asked questions about unique stays in Chicago, IL

  • What are some hidden gems to explore in Chicago, IL?

    For a hidden gem, check out the Museum of Contemporary Art Chicago. It's tucked away in a quiet part of the city and showcases some incredible modern art. Another great spot is the Garfield Park Conservatory, a stunning Victorian-era greenhouse with exotic plants from all over the world.
  • What attractions is Chicago, IL famous for?

    Chicago is known for its iconic architecture, like the Willis Tower (formerly Sears Tower) and the Wrigley Building. You can't miss Millennium Park, home to Cloud Gate, the famous bean sculpture, and the Crown Fountain. And of course, there's Navy Pier, with its Ferris wheel, shops, and restaurants.
  • What clothing or gear is recommended for the climate in Chicago, IL?

    Chicago has four distinct seasons. You'll need warm layers in winter, with temperatures often dropping below freezing. In summer, it can get very hot and humid, so pack light, breathable clothing. And don't forget a good raincoat, as Chicago is known for its unpredictable weather.
  • What are the best ways to travel to Chicago, IL eco-consciously?

    The most eco-friendly way to get to Chicago is by train. Amtrak offers direct routes from major cities, reducing your carbon footprint. If you're flying in, consider choosing an airline with a strong sustainability program. Once you're in the city, opt for public transport like the CTA or Divvy bike share.
  • Which neigbourhood offers the best unique stays in Chicago, IL?

    For unique stays, I'd recommend checking out the Wicker Park or Bucktown neighbourhoods. They have a vibrant arts scene, cool independent shops, and a range of unique hotels and Airbnb options.
  • What should you know about unique stays in Chicago, IL before booking?

    Before booking a unique stay, it's always a good idea to read reviews from other travellers. This will give you a better idea of what to expect and ensure the property is right for you. It's also worth considering the location and proximity to public transport.

Popular destinations

Best Chicago, IL unique stays with a jacuzzi

Among the 74 accommodations in Chicago, IL, here are the 1 best unique accommodations with a jacuzzi

Jeffjack Heated Pool Penthouse In Chicago's West Loop - Chicago, IL
9.6 147 reviews

Jeffjack Heated Pool Penthouse In Chicago's West Loop

apartment, Chicago
This penthouse apartment is conveniently located in the centre of Chicago, within easy walking distance of Union Station, Willis Tower, and CIBC Theatre. The apartment consistently receives excellent ratings for its location, cleanliness, and overall experience, making it a popular choice for travellers.
The apartment has two bedrooms, comfortably accommodating up to six guests. Enjoy a range of amenities including a rooftop pool, fitness centre, and private parking, as well as a fully equipped kitchen and balcony with stunning city views.

Neighborhoods and points of interest in Chicago, IL

Best pet friendly Chicago, IL unique stays

Among the 74 accommodations in Chicago, IL, here are the 1 best pet friendly unique accommodations

Located On Beautiful And Quite Boulevard! - Chicago, IL
9.7 70 reviews

Located On Beautiful And Quite Boulevard!

bungalow, Chicago
This Wrightwood neighbourhood three-bedroom house is conveniently located near Healy Metra station, offering easy access to Chicago's city centre (a 24km train journey or 32km drive), O'Hare International Airport, and popular areas such as Lakeview and Wicker Park (both approximately 32km away).
The property boasts a spacious layout sleeping up to nine guests, features a fully equipped kitchen, a large garden with outdoor games and a gas barbecue, plus free on-street and adjacent parking; nearby amenities include Starbucks, Aldi, and Walmart.
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