Any Chicagoan will tell you that The Windy City is abundant with hidden gems. With Chicago’s booming social scene, you want to make sure you see more than Navy Pier and The Magnificent Mile on Michigan Avenue.
Knowing what to do is as equally important as knowing where to stay in Chicago. Similar to the scene of New York City, it’s bursting with a diverse set of neighborhoods, and each area offers something unique to travelers from all walks of life.
In former years, Chicago’s historic South Loop was a catalyst for Chicago tourism. Now, locals and tourists alike are traveling to Chicago neighborhoods with a little more zest like Wicker Park, Old Town, Bucktown, Chicago River North, and Lincoln Park.
As far as where to stay in Chicago, the Near North Side and North Side is your best option if you want an authentic Chicago experience. Here, you’ll discover the best of the city, including restaurants, bars, and entertainment.
I’ve searched through all of Chicago’s Airbnbs to find the best places to stay in Chicago, based on price, aesthetic and style, and location.
Where to Stay in Chicago: Best Chicago Airbnbs
This Instagram-worthy Airbnb Plus is located in Chicago’s Old Town. Guests are just miles away from Lake Michigan and classic Chicago activities such as Second City, which schooled famous SNL comedians like Amy Poehler.
The neighborhood itself is quite dreamy with Victorian-style homes. It’s the perfect staycation spot for a little bit of romance or to treat yourself to a charming urban-getaway.
Up to 2 guests // 1 bedroom // 1 bed // 1 bath. Prices from $120 per night. Check pricing and dates here.
This second space is the perfect accommodation for large groups. Multiple guests return to this loft because it’s clean, accessible, and family-friendly!
Located in Lincoln Park, this Airbnb Plus is near the Peggy Notebaert Nature Museum and the Lincoln Park Zoo, and the zoo is free admission. These hot spots are bustling with family-days and special events for adults.
Note: The loft bedroom requires the use of a ladder and is only three-feet high. Fun for kids or slumber parties!
Up to 8 guests // 2 bedrooms // 2 beds // 2 baths. Prices from $112 per night. Check pricing and dates here.
This cozy and bright Airbnb Plus is the perfect solution for a weekend getaway.
Located in Uptown, it’s in a central location where guests can easily walk to the red line (the main train line) or Lake Michigan. Additionally, this space is just a few miles away from Wrigley Field and Wrigleyville, home to the Chicago Cubs, and a vibrant nightlife.
The apartment is above a bar, which can get pretty lively at night. For the right type of guest, this is the perfect crash-pad for an adventure on Chicago’s north side!
Up to 2 guests // studio // 1 bed // 1 bath. Prices from $80 per night. Check pricing and dates here.
For large groups that don’t know where to stay in Chicago on a budget and in a comfortable space, then this next location is for you!
Considering the size of this trendy and well-lit apartment, the price is an absolute steal for a large group. This pristine Airbnb Plus is ideal for guests who prefer a spacious apartment.
Public transportation is nearby making it easy to get to the best restaurants and entertainment in Chicago.
Up to 10 guests // 3 bedrooms // 5 beds // 2 bath. Prices from $60 per night. Check pricing and dates here.
Any city-dweller can appreciate an apartment with a picturesque kitchen like the one in this Airbnb Plus! The entire space is great and the location is prime.
Bucktown’s up-and-coming-scene is the “New Lincoln Park.” However, this gem of a neighborhood is uniquely its own with a vibrant hub of culture.
The location is perfect for anyone who wants to explore indie boutiques, trendy cocktail bars, and restaurants. This modern apartment is located in a quiet location, but close enough to Bucktown’s upbeat social life.
Up to 4 guests // 2 bedrooms // 2 beds // 1 bath. Prices from $95 per night. Check pricing and dates here.
The artistic and bright decor in this flat reflects the liveliness of the neighborhood!
The apartment is situated in Boystown, one of the largest LGBT communities in the United States. This place is perfect for an energetic crowd that wants an unforgettable Chicago experience.
Bring your dance moves, because this location is just a brief walk from the most popular dance spots in Chicago!
Up to 4 guests // 2 bedrooms // 3 beds // 1 bath. Prices from $104 per night. Check pricing and dates here.
This stylish West Loop pad sits high above the city for those who want a chic stay in Chicago. The apartment is smaller but it has all the amenities needed for a comfortable stay.
Previous travelers love the convenience of the location. The apartment is central, which makes it easy for guests to head downtown and explore Chicago’s myriad of restaurants and entertainment.
Up to 3 guests // 1 bedrooms // 1 beds // 1 bath. Prices from $139 per night. Check pricing and dates here.
If you want your stay to be close to the airport, look no further than this colorful and spacious apartment! Besides being close to the airport, this apartment is a short train ride to Wicker Park.
This Airbnb Plus is surrounded by countless restaurants, coffee shops, clubs, indie stores, and entertainment, all within walking distance.
Up to 3 guests // 1 bedroom // 1 bed // 1 bath. Prices from $113 per night. Check pricing and dates here.
This bright and clean Airbnb Plus is a dream apartment! Situated in a vintage greystone building, this place has everything you need to enjoy a comfortable stay.
The historic surrounding community has something for everyone; contemporary restaurants, bars, and shops. For history enthusiasts, it’s a great location to discover homes and businesses as old as the city itself.
Up to 4 guests // 1 bedroom // 2 beds // 1 bath. Prices from $130 per night. Check pricing and dates here.
If you’re traveling with a group of four or more, and want to stay in an apartment with that classic city feel, then this is the spot for you!
The large windows, the sleek floors, and the modern style is only a part of what makes this apartment prime. This stylish pad is within walking distance to some of Wicker Park’s most trending spots.
Up to 7 guests // 2 bedrooms // 4 beds // 2 baths. Prices from $100 per night. Check pricing and dates here.
This Airbnb is accommodations goals! Here, guests can enjoy all the beautiful amenities including a shared terrace adorned with lights.
If you want to hang out like a Chicagoan, you’ll want to grab a few drinks and spend time on this beautiful rooftop with a city view.
The apartment itself is a cozy, dreamy Italian-inspired space. Perfect for a romantic weekend getaway or solo travel.
Up to 2 guests // studio // 1 bed // 1 bath. Prices from $107 per night. Check pricing and dates here.
Within the heart of the trendy River North is this modern apartment perfect for groups of up to three.
The apartment is close to some of Chicago’s most popular cocktail bars, including Three Dots and a Dash, a tropical speakeasy, and Celeste, a swanky art deco cocktail bar.
Up to 3 guests // 1 bedroom // 1 bed // 1 bath. Prices from $159 per night. Check pricing and dates here.
That’s my list of where to stay in Chicago! If you book one of these Airbnbs, tag me in a pic or Insta Story and show off your Chicago Airbnb. Happy travels!
Planning a trip to Chicago? Be sure to check out my other Chicago travel guides here.