Find unique places to stay in Chicago, IL

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

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • priceline
  • tripadvisor
  • tripcom
  • sonder
  • homestay
  • hostelworld
  • hotelscom
  • agoda
Chicago, IL unique stays
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

91 Unique places to stay in Chicago, IL

Best family friendly Chicago, IL unique stays

Among the 91 accommodations in Chicago, IL, here are the 2 best family friendly unique accommodations

The Grand Kimball Lodge, Logan Square, Sleeps 20 - Chicago, IL
10 2 reviews
Chicago, IL
05/01 – 28/02
$1707/nighttotal: $92178 (54 )

The Grand Kimball Lodge, Logan Square, Sleeps 20

5 2
apartment , Chicago
This Logan Square dwelling is centrally located in Chicago, offering easy access to attractions such as Michigan Avenue and Millennium Park, though precise distances aren't specified.
This spacious, two-storey loft apartment boasts 278 square metres of living space, featuring five bedrooms, four bathrooms, two kitchens, two living areas, three outdoor spaces and sleeps up to twenty guests; amenities include a sauna, foosball table and record player.
Chicago Bootlegger House Sleeps 10-20 - Chicago, IL
9.9 155 reviews
Chicago, IL
11/09 – 13/09
$3340/nighttotal: $6680 (2 )

Chicago Bootlegger House Sleeps 10-20

1 11
bungalow , Chicago
This six-bedroom house is located in a lively neighbourhood, just a short walk from Lake Michigan, Lincoln Park Zoo, Wrigley Field, and the Red Line train. It has received excellent ratings for location, cleanliness, and overall user experience.
This spacious property can comfortably accommodate up to sixteen guests and features a fully equipped kitchen, a private rooftop deck, and a range of entertainment options including a foosball table, vintage slot machine, board games, and a working fireplace.

Best Chicago, IL unique stays with a pool

Located On Beautiful And Quite Boulevard! - Chicago, IL
9.8 65 reviews
Chicago, IL
21/08 – 23/08
$552/nighttotal: $1104 (2 )

Located On Beautiful And Quite Boulevard!

1 7
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.

Frequently Asked Questions about unique stays in Chicago, IL

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

    For a unique experience, head to the Garfield Park Conservatory, a stunning glasshouse with exotic plants and flowers. If you're looking for a quirky art experience, visit the Museum of Contemporary Art Chicago, known for its thought-provoking exhibitions. For a peaceful escape, stroll through the Lincoln Park Zoo, home to a wide variety of animals.
  • What attractions is Chicago, IL famous for?

    Chicago is renowned for its iconic architecture, particularly the Willis Tower, formerly known as the Sears Tower, which offers panoramic city views. Another must-see is Millennium Park, home to the Cloud Gate sculpture, affectionately nicknamed 'The Bean', and the Crown Fountain, where visitors can interact with their own reflections.
  • What clothing or gear is recommended for the climate in Chicago, IL?

    Chicago's weather can be unpredictable, so pack for all seasons. In summer, you'll need light clothing and comfortable shoes for walking. During the colder months, layers are essential, including a warm coat, hat, and gloves. Remember an umbrella for the occasional rain shower.
  • What are the best ways to travel to Chicago, IL eco-consciously?

    The most eco-friendly way to travel to Chicago is by train. Amtrak offers direct routes from many major cities, reducing your carbon footprint. If you're driving, consider carpooling or using public transportation while in the city. Chicago's extensive public transport system is efficient and reliable.
  • Which neigbourhood offers the best unique stays in Chicago, IL?

    The West Loop neighbourhood is known for its trendy hotels and unique accommodations. You'll find stylish boutique hotels like the Soho House Chicago and the Ace Hotel, both offering a modern and eclectic atmosphere.
  • What should you know about unique stays in Chicago, IL before booking?

    Before booking a unique stay, check the location and accessibility. Some unique accommodations might be located in quieter areas, so consider your transportation needs. Also, check the amenities and services offered, as some unique stays might have limited facilities compared to traditional hotels.

Destinations nearby

Best Chicago, IL unique stays with a jacuzzi

Among the 91 accommodations in Chicago, IL, here are the 1 best unique accommodations with a jacuzzi

Entire Bungalow In Chicago - Chicago, IL
9.4 24 reviews
Chicago, IL
24/07 – 26/07
$474/nighttotal: $948 (2 )

Entire Bungalow In Chicago

1 5
bungalow , Chicago
This three-bedroom Chicago bungalow, ideally located near O'Hare International Airport and offering easy access to downtown Chicago (approximately 26km from the airport and 20km from the city centre), provides convenient accommodation for travellers.
Sleeping six guests, the self-catering property features a fully equipped kitchen, a private garden with parking, and simple self check-in via lockbox.

Neighborhoods and points of interest in Chicago, IL

Best pet friendly Chicago, IL unique stays

Among the 91 accommodations in Chicago, IL, here are the 3 best pet friendly unique accommodations

Chicago Bootlegger House Sleeps 10-20 - Chicago, IL
9.9 155 reviews
Chicago, IL
11/09 – 13/09
$3340/nighttotal: $6680 (2 )

Chicago Bootlegger House Sleeps 10-20

1 11
bungalow , Chicago
This six-bedroom house is located in a lively neighbourhood, just a short walk from Lake Michigan, Lincoln Park Zoo, Wrigley Field, and the Red Line train. It has received excellent ratings for location, cleanliness, and overall user experience.
This spacious property can comfortably accommodate up to sixteen guests and features a fully equipped kitchen, a private rooftop deck, and a range of entertainment options including a foosball table, vintage slot machine, board games, and a working fireplace.
The Grand Kimball Lodge, Logan Square, Sleeps 20 - Chicago, IL
10 2 reviews
Chicago, IL
05/01 – 28/02
$1707/nighttotal: $92178 (54 )

The Grand Kimball Lodge, Logan Square, Sleeps 20

5 2
apartment , Chicago
This Logan Square dwelling is centrally located in Chicago, offering easy access to attractions such as Michigan Avenue and Millennium Park, though precise distances aren't specified.
This spacious, two-storey loft apartment boasts 278 square metres of living space, featuring five bedrooms, four bathrooms, two kitchens, two living areas, three outdoor spaces and sleeps up to twenty guests; amenities include a sauna, foosball table and record player.
Located On Beautiful And Quite Boulevard! - Chicago, IL
9.8 65 reviews
Chicago, IL
21/08 – 23/08
$552/nighttotal: $1104 (2 )

Located On Beautiful And Quite Boulevard!

1 7
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.
©2026 cozycozy.com