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Airbnb
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.
Airbnb
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!
Bachelorette Parties
11 Bachelorette Party Ideas In Chicago, Illinois

Get to explore and experience the best out of Chicago and return home with great memories. Chicago is most popular for its stunning joint perfect for bachelorette parties with many party hotels. Some of the party ideas you can indulge in while you are here include hosting a party at a party house, summer house Santa Monica, brunch spots, day party, cute drink spots, spa day, group classes, Aire ancient baths, ace bounce and many other options. Instead of spending a lot of time searching for the best bachelorette party ideas, we have searched and picked the most popular and best bachelorette party ideas. Read this article and check out our top best bachelorette party ideas in Chicago, Illinois.
Hotels With Outdoor Pools
Top 8 Chicago Hotels With Outdoor Pools: Enjoy A Dip With A View

With a mix of large scale skyscrapers and beautiful parks, Chicago is a great holiday destination. Although known as the windy city, you can rest assured that this doesn't refer to the weather. On your first few days, if you want to sit and absorb the culture, you should head to the popular site of Millenium Park. With its grand open spaces, art and theatre and ice rink, you can easily spend a few hours here. For great views, head to the top of Willis building for panoramic cityscapes. For something a bit different, spend some time at the Navy Pier. This large pier has everything from fun rides, fantastic eateries and boutique shops. It's a great place to take children for a day out. So after all that walking around and exploring, we're sure that you'll want to rest your feet and relax. Now you can sit back, or float in this case, and let the world pass you by. Just for you, we've found the best hotels with relaxing outdoor pools, in Chicago, Illinois. Keep reading and book today to get yourself in the vacation mood.
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.
Farm To Table Restaurants
Top 10 Farm To Table Restaurants In Chicago, Illinois

Welcome to the third most populous city of the US, that lies on the shores of freshwater Lake Michigan, the famous Chicago. Chicago is predominantly known for its architecture, best seen in several iconic skyscrapers, but also its artistic side, noted in its art museums. In many streets of the chicest neighborhoods of Chicago, one will spot elegant dining venues, that are influenced by the farm to table movement, as is the case for other major US cities as well. The whole idea behind this movement is to serve farm fresh food, regionally sourced and sustainably grown. If you feel like supporting this idea and want to taste seasonably-driven delicacies, visit any of the following best farm to table restaurants in Chicago, USA, for a unique dining experience!
Day Trips From
9 Best Day Trips From Chicago, Illinois

Everyone knows that Chicago is a fun city to explore, but its Chicago’s location that makes this city such a great value for your time and money. Being in the northeast corner of Illinois, Chicago has easy access to northern Illinois, southern Wisconsin, and northwestern Indiana. Chicago is just an hour and a half drive from Milwaukee, and a three-hour drive to Indianapolis. In addition, Chicago provides a great deal of access to the great recreation that Lake Michigan provides during the warmer months of the year. Day trips from Chicago offer a variety of activities, including nature, theme parks, festivals, and more.
Hotels With Smoking Rooms
Top 10 Hotels With Smoking Room Near Downtown Chicago, Illinois - Updated 2025

Chicago is located on the shores of Lake Michigan and is one of the largest cities in the U.S. The city is famous for many things such as jazz music, Chicago-style pizza and the downtown, which is home to numerous tourist attractions. The Art Institute of Chicago in the downtown area is probably one of the most notable places frequented by tourists during their visit to Chicago. The architecture of the building itself attracts many people. You can't miss Millennium Park while in downtown Chicago. This park offers free admission and has a number of interesting things to check out, such as the Lurie Garden, Cloud Gate and the Crown Fountain. Being a popular tourist destination, downtown Chicago and the nearby areas offer a number of accommodation options. Check out the top hotels with smoking room near Downtown Chicago, Illinois.
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.
Unique Hotels
Top 11 Unique Hotels In Chicago, Illinois - Updated 2025

Chicago, Illinois, is one of the largest cities in the United States. Popular for world-class attractions, such as its skyscrapers and modern architecture, and vibrant and progressive culture, the city definitely has plenty to offer. Art Institute of Chicago is one of the top art museums with global works. Willis Tower and Tribune Tower are two of the skyscrapers that offer dramatic views of soaring towers and the skyline. Urban parks, such as Millennium Park and Burnham Park, are some of the reasons to visit Chicago, as these are the city's initiatives to protect green spaces. There are also many things to do for free here. Because of all these features, tourists will surely love exploring the vibrant city of Chicago. To start planning for your vacation, check out the top unique hotels in Chicago, Illinois.
5 Star Hotels
Top 10 5-Star Hotels In Chicago, Illinois

Chicago is widely regarded as one of the best big cities in the United States, with a perfect blend of iconic landmarks, a thriving food scene, and an inclusive spirit that will provide you with the ultimate vacation experience. The city is lined with varying architectural styles, evident in its landmarks such as The Willis Tower, which is one of the world's tallest buildings. Millennium Park's attractions include art exhibitions, interactive fountains, and the evocative Cloud Gate. If you prefer a stroll along the water, you should visit the Chicago Riverwalk. Your trip to Chicago will not be complete unless you try their mouthwatering culinary specialties, such as the famous Chicago-style hotdogs. Your itinerary will undoubtedly be jam-packed with incredible sights to see and activities to enjoy, so make sure to book an excellent hotel to revitalize you. For great options, continue reading for the top 5-star hotels in Chicago, Illinois.
Gay Friendly Hotels
10 Best Gay-Friendly Hotels In Chicago, Illinois

Are you planning a trip to Chicago with your loved one? You can pack so much fun into your schedule. The city is home to numerous neighbourhoods, each offering something unique. Northalsted, also known as Boystown, is filled with welcoming people, great shops and restaurants. You can even follow The Legacy Walk to know more about the contributions of the LGBTQ+ community. Round up your day with a Blue Man Group performance at Briar Street Theatre or with a fun meal at Kit Kat Lounge & Supper Club. If dancing is on the cards, you can make your way to Roscoe’s Tavern or Sidetrack. You even have a wide variety when it comes to accommodations in Chicago. For options, take a look at this list of the best gay-friendly hotels in Chicago, Illinois.
Airbnb Tiny House
3 Best Airbnb Tiny Houses Near Chicago, Illinois

Chicago is known for its picturesque skyline and iconic landmarks. It offers many opportunities for you to admire the city views, particularly at 360 CHICAGO and Skydeck Chicago. If you're a lover of culture, you can marvel at public art in Millennium Park and join exciting activities and events for all ages. Families with kids can have a meaningful time at Adler Planetarium, Museum of Science and Industry, Chicago, and Shedd Aquarium. To learn more about African-American heritage, you can drop by The DuSable Black History Museum and Education Center. If you are traveling alone or with a friend or significant other, you might enjoy a unique stay in a tiny house. Check out the best Airbnb tiny houses near Chicago, Illinois, below.
Things To Do
8 Best Things To Do In West Chicago, Illinois

Chicago is famed for its rich history, stories of gangsters and sports fans. There are so many things to do in Chicago that it can be hard to know where to start! In order to get a comprehensive view of the city, this guide will take you through the eight best things to do in West Chicago, Illinois.
Hotels With Restaurants
Top 10 Hotels With Restaurant In Chicago, Illinois

Chicago, Illinois, is a popular tourist destination in the United States, famed for its modern architecture and beautiful lakes. When visiting Chicago, you can check out the artsy Millennium Park, for some Instagrammable street art, the gorgeous Navy Pier, for a day by the beach and the modern Art Institute of Chicago, for beautiful pieces of jewellery and decoration. After a long day of sightseeing, many tourists prefer the comfort and convenience of dining at their place of accommodation, rather than braving the crowds and traffic to find another eating spot. Below are 10 hotels with restaurants in Chicago, Illinois, that you should check out.
Vrbo
10 Best Vrbo Vacation Rentals Near The Navy Pier, Chicago, Illinois

Is the Navy Pier listed on the top of your list of Chicago must-sees? The Navy Pier is one of Chicago's best-known landmarks. It draws hundreds to thousands of tourists every day, so it can get really crowded especially during long weekends and holidays. To help you beat the crowd and make sure you enjoy every inch of the Navy Pier without much stress, we highly suggest staying near this well-known attraction. We scoured the whole city for 10 amazing vacation rentals that are located minutes away from the Navy Pier. These properties range from compact condos perfect for couples to spacious penthouse suites. Here are the best Vrbo accommodations near the Navy Pier, Chicago.
Vrbo
16 Best Vrbo Vacation Rentals In Chicago Old Town, Illinois

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.
Vrbo
14 Best Vrbo Vacation Rentals Near Chicago Lakefront, Illinois

Chicago is well-known as the 'Windy City' due to its windy weather. It's the home of deep-dish pizza. It also has many beautiful lakes. Major attractions in the city include the Fields Museum of Natural History, the Museum of Science and Industry, the Shedd Aquarium, and the Navy Pier, among others. The city is also famous for its history during Prohibition, the time when alcohol consumption and production was banned (except for religious purposes) since it was home to many famous gangsters, illegal speakeasies, and many other places where people who did not approve of Prohibition would find ways to go around it. Also, Chicago was home to the flapper culture of the Roaring Twenties, pre-Depression. However, before you can experience the wonders of Chicago, you have to be able to book the best accommodations. Check out the best Vrbo vacation rentals near Chicago Lakefront, Illinois.

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