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45 Best Airbnb Vacation Rentals In Downtown Chicago, Illinois

Known for its Bean in the Millennium Park, the downtown area of Chicago, Illinois surely has the glitz and glamour of the surrounding buildings and sights to see such as the Navy Pier and Art Institute. There's plenty of things to do in downtown Chicago, including hanging out at the hippest rooftop bars in the area. But what can it offer when it comes to vacation rentals for your next vacation in Chicago? Scroll down and check out the best Airbnbs in Downtown Chicago, Illinois.
Airbnb
12 Best Airbnb Vacation Rentals With A Hot Tub In Chicago, Illinois

Being the most populous city in Illinois, Chicago is a lakefront city that is famous for the best hotdogs and pizza in America. It offers miles and miles of shoreline and beautiful beaches that are a haven for people seeking to cool down during summer. Chicago boasts clear blue waters tourists and locals can appreciate. The Chicago School and Prairie School architecture, the first distinct American architectural style can be found in this city. Museums for kids and adults as well as art galleries can also be found in this amazing city. Discover many restaurants that have earned Chicago the reputation of being the best city to eat in America. Elevate your experience and check out the best Airbnb vacation rentals with a hot tub in Chicago, Illinois.
Airbnb
Top 24 Airbnb Vacation Rentals In Hyde Park, Chicago, Illinois

Situated on the eastern side of Chicago, Hyde Park is a small area that's home to around 30,000 people. Hyde Park has a lot to offer travelers with its numerous historical, scientific, and modern attractions. In the western area of Hyde Park, travelers will be able to find the Washington Park and the Art Institute of Chicago. Near Lake Michigan on the east, you will find the Museum of Science and Industry. Various shopping districts are found all around Hyde Park, which includes 53rd, 55th, and 57th streets. Whether it’s viewing the many different attractions, experiencing the local history, or simply enjoying the comfort of a staycation, check out these top Airbnb vacation rentals in Hyde Park, Chicago that will surely take care of all your needs while you stay in this part of Illinois.
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12 Best Airbnb Vacation Rentals Near Ukrainian Village, Chicago

The Ukrainian Village is a small but exciting place to visit and experience. Near Chicago's West Side, this region boasts many attractions, shops, bars and restaurants, and is the fastest growing neighborhood in the city. If you are looking for a piece of first-hand knowledge and experience of Eastern European, Polish and Ukrainian food, entertainment and culture, this place is a must visit. Explore the cultural and live music centers, museums, stunning cathedrals, churches and much more. This area also has a wide variety of accommodation in which you can unwind as you explore its offerings. Regardless of your preference and budget, check out these charming top Airbnb vacation rentals near Ukrainian Village, Chicago, and have a memorable vacation.
Airbnb
Top 10 Airbnb Vacation Rentals In Illinois, USA - Updated 2025

Illinois not only sits at the heart of the United States but is in itself a state of firsts. This is where the very first skyscrapers were erected. It is also the very first state to have a Ferris wheel. The presence of world-class museums, great foods, incredible sights, beautiful state parks, and an enticing culinary diversity are some of the few reasons that make it one of the most visited states in the United States. If you intend to visit any part of this beautiful state, proper accommodation is imperative if you desire to leave with an overall pleasant experience. Scroll down to take a look at our recommendations on the top Airbnbs in Illinois, USA.
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12 Best Airbnb Vacation Rentals In Andersonville, Chicago

Chicago is a world-class city known for neighborhoods that each offer a unique charm. Andersonville, on Chicago's north side, is traditionally a Swedish-immigrated area. The Andersonville Swedish Museum is here, as well as quaint stores such as the Svea Restaurant which serves lingonberries and meatballs. Although this nod to Chicago's history is just one reason to visit, Andersonville is also close to Lake Michigan and is home to the main street that touts small, locally owned businesses. Jumping on the El—Chicago's elevated train system—is easy from Andersonville, which takes you downtown. When visiting Andersonville, make sure you have a sweet home to stay in to make your visit the most relaxing possible. Check out these best Airbnb vacation rentals in Andersonville, Chicago, and begin planning your trip to the Windy City today!
Airbnb
Top 11 Airbnb Vacation Rentals In Chicago, USA

Welcome to Chicago, a city full of history and home to excellent food. Museum buffs will love the Art Institute of Chicago, Museum of Science and Industry and The Field Museum among others. Alternatively, spend a day at Millennium Park and Cloud Gate and ignite your senses with various sights, smells, sounds and tastes. Moreover, Chicago’s music, film, theater and comedy, have shaped much of American culture into what it is today. Come take a trip to the Windy City and see what it has to offer! Here are some great Airbnbs for both couples and solo travellers alike:
Airbnb
13 Best Airbnb Vacation Rentals In Downtown Chicago, Illinois - Updated 2025

Whether you are travelling to see parks, national landmarks, museums or just craving to have a night out with a view of an amazing skyline, Chicago in Illinois is the place for you! With its beautiful landscape and scenic lakeshores, you won't be lost. Chicago is home to many towering skyscrapers and friendly people. It even has hundreds of hotel properties and ample accommodation for a restful vacation. This third-largest city in the U.S. is proud of its diverse culture, making it very friendly to tourists and visitors alike. This place has numerous things to do for people of all ages, so whether it's a family vacation or you're going solo, here are some of the best Airbnb vacation rentals in downtown Chicago, Illinois.
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15 Best Airbnb Vacation Rentals Near Art Institute, Chicago

Chicago has lots of things to do for new tourists as well as those looking forward to revisiting. It is famous for its skyline which features striking buildings and skyscrapers with beautiful architecture, like the John Hancock Center and the Willis Tower. Another must-visit attraction here is the Art Institute of Chicago, which is known as the United States' oldest and largest museum. Apart from the attractions and the architecture, the city also boasts luxurious and comfortable vacation homes. In case you’re wondering where you should stay during your visit, then read on to discover the best Airbnb vacation rentals near Art Institute, Chicago.
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14 Best Airbnb Vacation Rentals Near South Side, Chicago

Chicago is the most populous city in Illinois and the third most populous city in the entire country! It is an internationally renowned city, known for its openness to diversity - in fact, the Windy City was host to an estimated 58 million domestic and international travelers in 2018 alone! It is home to beautiful lakes, shopping malls, theme parks, and delicious pizza places. Whether you’re traveling with your business colleagues for a conference, visiting a relative in the city, or even just wanting to explore this fascinating city on a solo trip, the accommodation options are as infinite as the things you can do in this city! Read on for the best Airbnb vacation rentals near South Side, Chicago.
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15 Best Airbnb Vacation Rentals Near McCormick Place, Chicago

Chicago is one of the largest cities in America and is home to tons of amazing things like museums, highly-rated restaurants with a view, art galleries, shows, entertainment, sports, and even McCormick Place, the largest convention center in North America. The building consists of four interconnected buildings and an indoor area sitting on the shores of Lake Michigan. It is close to Chicago's public transit and is home to annual events such as the National Restaurant Association Show and the Chicago Auto Show. If you are planning to attend an event there soon, stay at a nearby hotel or vacation rental. Scroll down to check out some of the best Airbnb vacation rentals near McCormick Place, Chicago.
Airbnb
8 Best Airbnb Vacation Rentals Near Bucktown, Chicago

Bucktown is well-known for its trendy reputation, thanks to the abundance of shopping spots in Chicago. Also, Bucktown is a heritage spot because it has been settled by many immigrants, especially Polish refugees from the many Partitions of Poland, as well as later Polish refugees who fled the persecution of the Poles during the Second World War. Other than the history, Bucktown and the nearby Wicker Park are known for their famous art galleries and their vibrant nightlife, including the famous restaurants. Here are some of the best places to stay when visiting the amazing places of Bucktown and Wicker Park. So, what are you waiting for? Read on to learn about the best Airbnb vacation rentals near Bucktown, Chicago.
Airbnb
17 Best Luxury Airbnb Vacation Rentals Near Old Town, Chicago

Old Town, as its name implies, is one of the oldest neighborhoods in Chicago. To learn more about the area's past, head over to Chicago History Museum. Another stop you can take is the stunning St. Michael Church, which was built back in 1869 and is easily identifiable thanks to its tall spire. Old Town Ale House is the place to be, especially since Anthony Bourdain called it the best dive bar in the city. If you prefer sweets over alcohol, you can visit Fudge Pot. Meanwhile, if you love comedy, The Second City is worth a stop as this comedy club is known for launching the careers of famous comedians such as Tina Fey, Steve Carell, and Mike Myers. There is so much to see and do in this area. Read on for the best luxury Airbnb vacation rentals near Old Town, Chicago, to give yourself time to see these wonderful attractions.
Airbnb
12 Best Airbnb Vacation Rentals Near Edgewater, Chicago

Chicago provides one of the best apartments around where they are conveniently located near either the subways or the nearest transportation system. They have a range of apartments - from modern and chic to vintage looking - but one thing is for sure, is that they all are cosy and the hosts make sure the stay is a good and unforgettable one. It is also true that these Airbnbs are often strategically located near supermarkets which makes grocery runs a quick and fuss-free one. Airbnb vacation rentals in Andersonville see a lot of visitors, but the neighborhood next to it, Edgewater, also has some amazing places to stay. Find out where to head to for affordably priced accommodations when in Edgewater. Scroll below to check out the best Airbnb vacation rentals near Edgewater, Chicago.
Airbnb
12 Best Airbnb Vacation Rentals Near Pilsen, Chicago

Chicago’s Pilsen Historic District is a vibrant multicultural residential neighbourhood steeped in art and culture. From striking murals that adorn the area to the various museums and galleries there, Pilsen has an artistic vibe that makes it special. Its rich immigrant history - Eastern European followed by Mexican - has resulted in an infusion of these cultures into the area by way of art institutions like Thalia Hall and the Mexican Museum of Art, and a range of top-notch cafes, bars, and restaurants. And what’s more, this hip neighbourhood is just 15 minutes away by train from the best pizza places in Chicago downtown! There is a great variety of street food you must try in Chicago as well. To help you find the perfect place, here’s our list of the best Airbnb vacation rentals near Pilsen, Chicago.
Airbnb
Top 14 Airbnb Plus Homes In Chicago, US

Chicago has so much to offer, both for business and for pleasure. With its stunning skyline, nice beaches, and interesting museums there is plenty to see on a visit here. Take a walk through Millenium park to soak up some greenery and view the shiny "bean" sculpture; Wander out to Navy Pier to experience a lively evening atmosphere, with carnival rides! The Art Institute of Chicago, Field Museum of Natural History and Lincoln park zoo all offer something unique. Whatever your interests, Chicago has something for you! And whether you're looking for chic apartments or mansions for rent in Chicago, Airbnb has you covered. So if you are planning a visit, be sure to take a look at these top 14 Airbnb Plus homes in Chicago, US to make your stay as good as possible.
Airbnb
10 Best Airbnb Near Douglas Park, Chicago

Douglas Park, a neighborhood in Chicago, beckons visitors with a cornucopia of entertainment options. For the inquisitive and culturally-minded, National Museum of Mexican Art is a veritable treasure trove of Mexican culture and heritage. Families with little ones can embark on a watery adventure at the nearby Shedd Aquarium, an aquatic wonderland brimming with exotic marine life and interactive exhibits. For tourists who want to enjoy the city's lively nightlife, the pulsating Pilsen neighborhood has a wide range of artistic and cultural activities, including a mix of galleries, theaters, and music venues. Planning to visit soon? Keep reading to see the best Airbnb near Douglas Park, Chicago.

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