Search unique places to stay in Chicago from 100+ sites!

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

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

74 Unique places to stay in Chicago

Explore Family-Friendly Unusual Accommodations in Chicago

Kid-friendly unique stays in Chicago offer memorable environments where both kids and parents can truly relax.

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

Tiny Cozy Guesthouse In Quiet Family Neighborhood

cabin, Dunning
This Chicago-area cabin, perfect for families, is located [Insert Specific Neighborhood/Area in Chicago and Distance to Landmark, e.g., in the suburbs, approximately 30 miles from downtown Chicago and 10 miles from the Magnificent Mile].
This pet-friendly 2-bedroom, 1-bathroom cottage sleeps four, features a kitchen with a fridge and microwave, air conditioning, parking, and internet access.
Chicago Bungalow Near Wrigley Field W/ King Suite - Chicago
9.7 273 reviews

Chicago Bungalow Near Wrigley Field W/ King Suite

bungalow, Chicago
This Chicago home is located in a safe and family-friendly neighborhood, just a short distance from pubs, restaurants, and Wrigley Field. It consistently receives excellent ratings for location, cleanliness, and user experience. This comfortable bungalow features three bedrooms and two bathrooms, comfortably sleeping up to nine guests. Amenities include a fully equipped kitchen, a private backyard, fast internet, and air conditioning, making it perfect for families or groups of friends exploring Chicago.
Chicago Bootlegger House Sleeps 10-20 - Chicago
9.9 160 reviews

Chicago Bootlegger House Sleeps 10-20

bungalow, Chicago
This historic bungalow in Chicago's Lakeview neighborhood offers a unique stay for travelers seeking a spacious and entertaining vacation rental. With excellent user and location ratings, this 6-bedroom, 2-bathroom property can accommodate up to 16 guests.
The bungalow features a private rooftop deck, a foosball table, a vintage slot machine, multiple 85-inch TVs, and a fully equipped kitchen. It also has a large dining area, comfortable furnishings, and a working fireplace, making it a perfect place for families and groups to relax and enjoy their stay in Chicago.

Our Favorite Unique Stays with a Pool in Chicago

A unique stay in Chicago with a pool means enjoying a swim in a truly one-of-a-kind setting.

Chicago Bungalow Free Parking Garage By Downtown - Chicago
9.8 83 reviews

Chicago Bungalow Free Parking Garage By Downtown

bungalow, Chicago
This three-bedroom, one-bathroom Chicago cottage is located in the quiet Bridgeport neighborhood, a short walk from the 62 bus and subway lines and a short drive from Chinatown, Millennium Park, and McCormick Place.
The single-story house, offering free parking in a two-car garage plus street parking with a permit, comfortably sleeps six guests and features a fully equipped kitchen (fridge, freezer, microwave), air conditioning, a garden, and step-free access.

Frequently Asked Questions about unique stays in Chicago

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

    For a unique experience, head to the Garfield Park Conservatory, a stunning indoor garden with a diverse collection of plants. If you're looking for some history, check out the Chicago Cultural Center, a beautiful building with free exhibits and events. And for a taste of the city's past, take a stroll through the historic neighborhoods of Ukrainian Village or Pilsen.
  • 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 the Magnificent Mile, a stretch of Michigan Avenue lined with shops and restaurants. And of course, no trip to Chicago is complete without a visit to Navy Pier, a bustling entertainment complex with a Ferris wheel, restaurants, and shops.
  • What clothing or gear is recommended for the climate in Chicago, IL?

    Chicago's weather can be unpredictable, so pack layers! You'll need a warm jacket, hat, and gloves for the winter months, and a light jacket or sweater for the spring and fall. Remember to bring comfortable shoes for walking, as you'll be doing a lot of exploring.
  • What are the best ways to travel to Chicago, IL eco-consciously?

    The best way to get around Chicago sustainably is by using public transportation. The CTA (Chicago Transit Authority) has an extensive network of buses and trains that can take you almost anywhere in the city. You can also consider renting a Divvy bike for a fun and active way to explore.
  • Which neigbourhood offers the best unique stays in Chicago, IL?

    For a unique stay in Chicago, you'll want to check out the West Loop neighborhood. It's home to trendy hotels like the Soho House Chicago, a private members' club with a hotel attached, and the Ace Hotel Chicago, known for its stylish design and rooftop bar.
  • What should you know about unique stays in Chicago, IL before booking?

    When booking a unique stay in Chicago, it's important to consider your budget and the location. Some of these unique accommodations can be more expensive than traditional hotels, and their location might not be as central. It's also a good idea to read reviews from other guests to get a sense of the experience.

Popular destinations

Choose the Right Unique Stays with a Hot Tub in Chicago

A private hot tub at your unique stay makes every trip to Chicago truly unforgettable after a day in the city.

Chicago Bungalow Near Wrigley Field W/ King Suite - Chicago
9.7 273 reviews

Chicago Bungalow Near Wrigley Field W/ King Suite

bungalow, Chicago
This Chicago home is located in a safe and family-friendly neighborhood, just a short distance from pubs, restaurants, and Wrigley Field. It consistently receives excellent ratings for location, cleanliness, and user experience. This comfortable bungalow features three bedrooms and two bathrooms, comfortably sleeping up to nine guests. Amenities include a fully equipped kitchen, a private backyard, fast internet, and air conditioning, making it perfect for families or groups of friends exploring Chicago.

Neighborhoods and points of interest in Chicago

Best pet friendly Chicago unique stays

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

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

Located On Beautiful And Quite Boulevard!

bungalow, Chicago
This Chicago bungalow, located in the Wrightwood neighborhood, offers easy access to the Healy Metra station (5-minute drive) for a quick 15-minute train ride downtown, and is within 20 minutes of Lakeview, Wrigleyville, and O'Hare International Airport.
The three-bedroom, one-bathroom house sleeps nine guests and features a large living room with a 70" smart TV, a well-equipped kitchen, a spacious backyard with a gas grill, and is close to Kelvin Park, Starbucks, Aldi, and Walmart.
Chicago Bootlegger House Sleeps 10-20 - Chicago
9.9 160 reviews

Chicago Bootlegger House Sleeps 10-20

bungalow, Chicago
This historic bungalow in Chicago's Lakeview neighborhood offers a unique stay for travelers seeking a spacious and entertaining vacation rental. With excellent user and location ratings, this 6-bedroom, 2-bathroom property can accommodate up to 16 guests.
The bungalow features a private rooftop deck, a foosball table, a vintage slot machine, multiple 85-inch TVs, and a fully equipped kitchen. It also has a large dining area, comfortable furnishings, and a working fireplace, making it a perfect place for families and groups to relax and enjoy their stay in Chicago.
©2026 cozycozy.com