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Airbnb
45 Best Airbnb Vacation Rentals In Downtown Chicago, Illinois - Updated 2025
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.
Vacation Rentals With Private Pool
10 Best Vacation Rentals With Private Pool In Chicago, Illinois - Updated 2025
Picturesque buildings, award-winning museums, and lively entertainment scene are some of the best things you'll see on your trip to Chicago. But that's not all—this city is also a great place for art enthusiasts and foodies to explore. Here, you'll get to visit a number of art galleries showcasing traditional and modern local art, such as The Art Institute of Chicago and the Museum of Contemporary Art. Do not leave the city without tasting Chicago-style pizza pies and hotdogs. After exploring this urban destination, you would need to stay in a place where you can relax and unwind. Check out the best vacation rentals with private pool in Chicago, Illinois.
Party Houses For One Night
20 Best Party Houses For Rent In Chicago - Updated 2025
Are you looking for a place to hold a party in Chicago? If so, you will find many rentals in Chicago that will help make your dream party become a reality. But before you throw your party, you can take some time to explore how beautiful Chicago is. You will have many unique experiences while touring the "Windy City." You can take Instagram-worthy pictures at The Bean and go for a stroll at Grant Park. You can even catch a baseball game at Wrigley Field or visit a number of art galleries. If you feel hungry, you can grab a slice of pizza from Lou Malnati's Pizza or an Italian beef sandwich from Al's #1 Italian Beef. For dessert, have a chocolate marshmallow sundae from Margie's Candies. After a day of adventure, you can start planning your party. As you plan, check out some of the best party houses for rent in Chicago. **Popular nightclubs in Chicago** - **Smartbar**: Here's a club where you can always jam to some fresh music! The independent nightclub has been firing up its dancefloor for decades, and it's a great place to meet fellow music lovers and party people! - **Beauty Bar Chicago**: If you're looking for some themed parties, Beauty Bar's the place to be. Happy hours from 7pm - 9pm each night, and I'd love to be there if I'm ever in Chicago!
Cheap Airbnbs
19 Best Cheap Airbnbs In Chicago, Illinois - Updated 2025
Tourists will not run out of things to do in Chicago. From going on an architectural tour around the area and even getting a bird's eye view of the Windy City from Skydeck Chicago at the Willis Tower Skydeck or the Signature Room in Chicago 360 to watching a game at either the Wrigley Field or the US Cellular Field, there's really something for everyone there, regardless of what your interests may be. You can even catch a comedy gig at Second City or treat yourself to an Italian beef sandwich or a deep-dish pizza. The numerous attractions offered by Chicago, however, come at a price; the city is consistently ranked as one of the most expensive cities in the country. If you plan to visit the Windy City, there are several options for cheap Airbnbs in Chicago, Illinois, to choose from.
Airbnb
Top 24 Airbnb Vacation Rentals In Hyde Park, Chicago, Illinois - Updated 2025
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.
Mansion Rentals
9 Best Mansion Rentals In Chicago, Illinois - Updated 2025
Planning on going on a trip to Chicago soon? You can visit Millennium Park and the Museum of Science and Industry, or you can try walking on the sky deck at the Willis Tower while watching the city below your feet. If you want to explore, go on a river cruise and see the different significant buildings and beautiful architecture around Chicago. You can also simply walk along the streets and have some famous Chicago-style hotdogs. There are many non-touristy things to do in Chicago, so plan your trip well. If you are heading here with a large group, consider staying in a mansion for an upgraded experience. Read on for the best mansion rentals in Chicago, Illinois.
Airbnbs With Pools
27 Best Airbnbs With Pool In Chicago, IL - Updated 2025
The city of Chicago is famous all over the world, and it's not just because it is the third most populous city in the United States; it also stands out as a global leader and hub for finance, commerce, technology, telecommunications and transportation having some of the busiest airports in the world (O'Hare International Airport). Chicago is a world-class haven for the commercial, industrial and cultural sectors. The city on the shores of Lake Michigan is rich in top attractions in both the business world and the entertainment world. If it's business or fun that brings you to Chicago, you may need a place to stay for the short duration of your travel or journey. Don't know where to stay? Whether you're looking for a luxury apartment or an Airbnb with a private pool in Chicago, we've got you covered! Check out these best Airbnbs with pool in Chicago, IL.
Luxury Airbnb
14 Best Luxury Airbnb Vacation Rentals In Chicago, Illinois - Updated 2025
The third-largest city of the United States is not only an important commercial and industrial hub--it is also rich in culture, art, and cuisine. Music is among the important facets of the city, with house music, electronic dance music, jazz, rock, and blues keeping the scene alive. The city hosts eccentric festivals, the majority of which are centered around music, and has wide-ranging places to visit, from art galleries to skateparks. The architecture of the city is most impressive, with glorious skyscrapers that have been designed most impressively. Imagine staying in one of the luxurious penthouses with a view of the charming Chicago skyline! Well, the dream is very easy to reach. Scroll down to find some of the best luxury Airbnb vacation rentals in Chicago, Illinois. **Popular picks in Chicago** - Art lovers cannot miss out on visiting Art Institute of Chicago, which features a vast collection of artworks from prominent artists such as Renoir, Van Gogh, Monet, and others. - Millennium Park is the second largest visitor attraction in the city. It houses several spaces, such as a concert lawn, public art collections, a seasonal ice rink, an urban garden, a theater, and sculptural bridges. - Catch some of the best views of the city at 360 Chicago - TILT, an enclosed glass and steel platform that moves and is perfect for all thrill seekers.
Romantic Airbnb
4 Best Romantic Airbnbs In Chicago, Illinois: The Perfect Place For Romantics
Ah, The Windy City! When you step foot in vibrant Chicago, expect to be under its spell for a long, long time–especially if you're a lover of art and a lover in general. Some movies that were shot here include classic, swoon-worthy rom-coms such as *While You Were Sleeping* and *My Best Friend's Wedding*. So, you and your significant other can check out some of the shoot locations and maybe recreate a scene or two! What's special about Chicago is that it also boasts a rich history and contemporary offerings. It has everything for everyone, including enjoying an intimate spa experience at AIRE Ancient Baths Chicago or relishing drinks and sunset views at the lofty CloudBar at 360 Chicago. What are you waiting for? Plan your itinerary now and book any of the best romantic Airbnbs in Chicago, Illinois, for an amazing experience. We've also compiled a couple of fun activities for you and your beloved to try out: **Tours and activities for couples:** - Take gorgeous photos, learn interesting historical facts, and listen to amazing romantic stories on a walking tour of Chicago. - If you are looking for something more laid-back while still boasting a romantic atmosphere, book a Lake Michigan cruise. There's even a bar onboard if you'd like to toast to each other.
Airbnb Monthly
10 Best Airbnb Monthly Rentals In Chicago, Illinois - Updated 2025
Situated on Lake Michigan in Illinois, Chicago, also known as the Windy City, is one of the largest cities in the United States. It is notable for its amazing skyline that boasts some of the tallest skyscrapers in the country, including the Willis Tower and John Hancock Center. If you're interested in learning about the local history and art, you must include Museum of Contemporary Art and Oriental Institute Museum in your list of places to visit in Chicago. The city also has more to offer such as Jackson Park, Oak Street Beach, and Chicago Riverwalk, among others. Due to its vastness, Chicago is hard to explore within a few days. That's why tourists usually choose hotels with free parking in downtown Chicago or accommodations that offer monthly rentals. For quaint vacation homes, continue reading for the best Airbnb monthly rentals in Chicago, Illinois.
Airbnb
12 Best Airbnb Vacation Rentals With A Hot Tub In Chicago, Illinois - Updated 2025
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
12 Best Airbnb Vacation Rentals Near Ukrainian Village, Chicago - Updated 2025
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 Mansion
Top 5 Airbnb Mansions In Chicago, Illinois - Updated 2025
Chicago's ideal location on Lake Michigan provides the metropolis with a dramatic cityscape that visitors admire. Bold architecture dominates the bustling skyline, adding to the city's beauty. One of the most iconic of them is the 100-story John Hancock Center in the Magnificent Mile district, which has an observation deck - offering the most magical view of the city. Willis Tower also affords panoramic city views from its 103rd-floor deck. For travelers with an interest in art and culture, exploring the renowned Art Institute of Chicago is a must. You can also enjoy a family day at Millennium Park. If you're into fabulous, over-the-top vacation rentals that guarantee a luxurious stay, browse through this list of the top Airbnb mansions in Chicago, Illinois, for a memorable holiday.
Airbnb
14 Best Airbnb Vacation Rentals Near South Side, Chicago - Updated 2025
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.
Airbnb
15 Best Airbnb Vacation Rentals Near McCormick Place, Chicago - Updated 2025
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.
Vrbo
16 Best Vrbo Vacation Rentals In Chicago Old Town, Illinois - Updated 2025
Old Town is Chicago’s one of the most historic districts. It is known for its lovely Victorian-era architecture, tree-lined streets and is home to St. Michael’s Church, one of the seven buildings to survive the Great Chicago Fire in 1871. You will also find eclectic coffee shops, quirky boutiques, mom and pop shops, and charming eateries around every corner of the town. Though this town is cocooned away from the hustle and bustle of downtown Chicago, there is plenty to enjoy within walking distance. Lincoln Park Zoo, North Avenue beach, The Second City theater, Oak Street, and Michigan Avenue can be reached by walk. There are over 103 restaurants in and around the town, bars and lounges are abundant on Wells and Magnificent Mile is home to numerous shops. If you are in Chicago and are looking for a place to stay, the Old Town should be your best bet. Here are the best Vrbo accommodations in Chicago Old Town, Illinois.
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.
Airstream Rental
4 Best Airstream Rentals In And Near Chicago, Illinois
Chicago is one of the United States' largest cities, and it's packed with endless things to experience. Located on the shores of Lake Michigan, this city has an intriguing past filled with bygone-era gangsters, covert speakeasies, and smooth jazz music. Big attractions include architectural gems such as John Hancock Center and the neo-Gothic Tribune Tower. For art lovers, there's The Art Institute of Chicago. But even city dwellers need an escape from bustling metropolitan life, and spiffy Airstream trailers provide an easy way to hit the open road. If you're ready to explore Illinois's scenic plains and beyond, then you must scroll down to see the best Airstream rentals in and near Chicago, Illinois.
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