The widest selection of unusual accommodations in Chicago, IL

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

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Chicago, IL unique stays
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

74 Unique places to stay in Chicago, IL

Discover Central Unique Stays in Chicago, IL

Position yourself steps away from famous independent bistros and transit links with central unique stays in Chicago, IL.

Beverly Hills Of Chicago Luxury Guest Favorite - Chicago, IL
9.9 41 reviews

Beverly Hills Of Chicago Luxury Guest Favorite

bungalow, Chicago
This five-bedroom Chicago bungalow is located in the Beverly Hills neighbourhood, a 24km train journey from Chicago's city centre.
Sleeping up to 12 guests, this self-catering house boasts a fully-equipped kitchen, three-and-a-half bathrooms, a games room with pool table and air hockey, private deck, and parking; close to local shops and restaurants.
3br Home W/ Free Driveway Parking | Near Chicago - Chicago, IL
10 285 reviews

3br Home W/ Free Driveway Parking | Near Chicago

bungalow, Berwyn
This Berwyn bungalow, situated in a peaceful neighbourhood approximately 32km from downtown Chicago, offers easy access to the city's attractions.
The three-bedroom, one-bathroom house sleeps six guests and boasts a recently remodelled modern interior, including a fully equipped kitchen, air conditioning, free private parking, and all amenities on one floor.
Historic Hales Mansion Near Frank Lloyd Wright - Chicago, IL
10 8 reviews

Historic Hales Mansion Near Frank Lloyd Wright

castle, Oak Park
This Tudor Revival mansion, situated in North Oak Park within walking distance of Oak Park's town centre, offers a unique castle-like experience.
Sleeping up to 16 guests, this four-bedroom, three-bathroom property boasts a performance hall, formal dining room, jacuzzis, four fenced second-floor porches, on-site parking for three vehicles, and event catering equipment (100 chairs, 100 place settings), with additional rooms and beds available on request; all proceeds benefit the Language and Music School's scholarship fund.
Chicago Bootlegger House Sleeps 10-20 - Chicago, IL
9.9 164 reviews

Chicago Bootlegger House Sleeps 10-20

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.

Explore Family-Friendly Unique Stays in Chicago, IL

Book a family-friendly unique stay in Chicago, IL near city attractions for a holiday that truly stands out.

Chicago Bootlegger House Sleeps 10-20 - Chicago, IL
9.9 164 reviews

Chicago Bootlegger House Sleeps 10-20

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.

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 a great place to see some modern art. Another great place is the Garfield Park Conservatory, a beautiful greenhouse with a variety of plants and flowers.
  • What attractions is Chicago, IL famous for?

    Chicago is famous for its iconic architecture, like the Willis Tower and the John Hancock Center. You can't miss the Magnificent Mile, a stretch of North Michigan Avenue with high-end shops and restaurants. And of course, you'll want to visit Navy Pier, a popular spot for amusement rides, restaurants, and entertainment.
  • What clothing or gear is recommended for the climate in Chicago, IL?

    Chicago weather can be unpredictable, so pack layers. You'll need a warm coat, hat, and gloves for the winter months, and a light jacket or sweater for the spring and autumn. Remember comfortable shoes for walking, as you'll be exploring the city on foot.
  • What are the best ways to travel to Chicago, IL eco-consciously?

    The best way to get around Chicago is by public transport, the 'L' train is a great way to get around the city, and it's very efficient. If you're coming from outside the city, consider taking the train or bus. You can also rent a bike for a more eco-friendly way to explore the city.
  • Which neigbourhood offers the best unique stays in Chicago, IL?

    The West Loop is a great neighbourhood for unique stays, with its trendy hotels and chic lofts. You'll also find a lot of cool bars and restaurants in the area.
  • What should you know about unique stays in Chicago, IL before booking?

    Before booking a unique stay, check the reviews and make sure it's in a safe and convenient location. You'll also want to consider the amenities and services offered, as well as the size and type of accommodation.

Popular destinations

Our Favourite Unique Stays with a Hot Tub in Chicago, IL

Relax after a busy city day with a secluded hot tub at your premier unique stay in Chicago, IL.

Hilton Garden Inn Chicago/oakbrook Terrace - Chicago, IL
8.3 24 reviews

Hilton Garden Inn Chicago/oakbrook Terrace

hotel, Oakbrook Terrace
The Hilton Garden Inn Chicago/Oakbrook Terrace is situated in Oakbrook Terrace, Illinois, offering convenient access to local attractions without being in a busy downtown area.
This 3-star hotel provides guests with complimentary internet, an on-site restaurant and bar, a swimming pool, a hot tub, and a fitness centre, alongside parking and a shuttle service.

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 3 best pet friendly unique accommodations

Chicago Bootlegger House Sleeps 10-20 - Chicago, IL
9.9 164 reviews

Chicago Bootlegger House Sleeps 10-20

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.
Your Second Home In Chicago - Chicago, IL
9.9 28 reviews

Your Second Home In Chicago

bungalow, Chicago
This Chicago bungalow, situated a short 8km drive from Lake Michigan, offers convenient access to the lakefront and its recreational activities.
Sleeping up to 10 guests, this three-bedroom, 1.5-bathroom house boasts ample parking, modern furnishings, and a fully equipped kitchen including a fridge, freezer and microwave; internet access and air conditioning are also included.
Historic Hales Mansion Near Frank Lloyd Wright - Chicago, IL
10 8 reviews

Historic Hales Mansion Near Frank Lloyd Wright

castle, Oak Park
This Tudor Revival mansion, situated in North Oak Park within walking distance of Oak Park's town centre, offers a unique castle-like experience.
Sleeping up to 16 guests, this four-bedroom, three-bathroom property boasts a performance hall, formal dining room, jacuzzis, four fenced second-floor porches, on-site parking for three vehicles, and event catering equipment (100 chairs, 100 place settings), with additional rooms and beds available on request; all proceeds benefit the Language and Music School's scholarship fund.

Check Out Unique Stays with a Pool in Chicago, IL

Enjoy an urban dip from a unique stay in Chicago, IL with a pool, right in the city centre.

Hilton Garden Inn Chicago/oakbrook Terrace - Chicago, IL
8.3 24 reviews

Hilton Garden Inn Chicago/oakbrook Terrace

hotel, Oakbrook Terrace

Handpicked Luxury Unique Stays in Chicago, IL

These luxury unique stays in Chicago, IL offer a sophisticated urban base with a singular twist.

3br Home W/ Free Driveway Parking | Near Chicago - Chicago, IL
10 285 reviews

3br Home W/ Free Driveway Parking | Near Chicago

bungalow, Berwyn
©2026 cozycozy.com