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Staycation
Top 10 Staycation Spots In Chicago, Illinois

Chicago, often called the Windy City, is a multi-layered metropolitan. There is much to experience here from sports, endless skyscrapers, the best of modern architecture, local fast-food joints, a host of Michelin-starred restaurants, famous spots like The Bean, walking trails on Lake Michigan shoreline, parks, museums, and much more. In addition, there is a festival here for everyone! Whether you like blues music or jazz, stamp collecting or world cinema, martial arts or political discourse, you'll find an event or a festival to suit your taste. Lose yourself in the charms of the Windy City. You'll find that it wins your heart with its underrated charm. And, to make your travel planning easier, here is a list of the top staycation spots in Chicago, Illinois.
Vrbo
9 Best Vrbo Vacation Accommodations In Chicago's Magnificent Mile

When you visit the Windy City, Chicago, there are many areas that you can choose to stay in. One of the most unique ones is the Magnificent Mile, an upscale section of the city, in the centre of the shopping section and next to the Gold Coast, offering many attractions and things to do at night. In this area, you may find luxurious and high-end accommodations, suitable for both tourists or professionals staying for a few weeks or even a couple of months. We did a thorough search and offer you this list of the best Vrbo accommodations in Chicago's Magnificent Mile.
Things To Do
39 Best Things To Do In Downtown Chicago, Illinois

Chicago, Illinois, is a city bustling with life and energy. With its glassy skyscrapers and rocking festivals, this windy city will figuratively blow your mind! But don't be fooled by its modernity. The city’s art museums have just the right amount of old in their new that continues to amaze locals and travelers alike. When you are done exploring the artsy side of the city, don't forget to indulge in its diverse culinary scene. The accommodation choices are just as pleasing, especially in the downtown area! From historic hotels featuring timeless elegance to fully equipped Airbnb vacation rentals, the bustling heart of the city is brimming with options. Downtown Chicago is so versatile that there is something for everyone. But don't be overwhelmed by all these options. Read this article to know about some of the best things to do in downtown Chicago, Illinois.
Desserts
10 Best Sweets And Dessert Spots In Chicago, Illinois

"Second City", "City of the Big Shoulders", "Windy City", Chicago is an all-encompassing and all-embracing fusion of the commercial, industrial, and cultural. America's heartland and a major metropolitan city, the vibe of the city exudes warmth, imagination, and confidence in every aspect. Considered as a city in a garden – or, "Urbs in Horto" – the dreamy landscape of Chicago, bordered by the vast Lake Michigan on one side and high-rising skyscrapers on the other, attracts all who set their foot to discover the city, but eventually end up falling in love with it. So, while you're in the city, add a note of sweet sin by indulging in some heavenly desserts in Chicago. Scroll below for the best sweets and dessert spots in Chicago, Illinois.
Romantic Places
10 Best Romantic Places In Chicago, Illinois

Chicago is located in the state of Illinois and it is the third largest city in the United States. It sits in Lake Michigan, one of the nation’s Great Lakes. Known for its architecture, the city boasts some impressive buildings, including the Willis Tower (formerly known as the Sears Tower) and the John Hancock Center. This large Midwest city offers plenty of attractions to explore, especially if you’re enjoying a romantic getaway. You and your partner can check out the Impressionist artwork at the Art Institute of Chicago. Take selfies in the reflection of “The Bean”, a public sculpture in Millennium Park. Or cuddle up on the Ferris wheel at Navy Pier. We’ve put together a list of our favourite romantic places in Chicago, so read on and check out the options.
Airbnb
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
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.
Hotels With Hot Tubs
Top 14 Hotels With Hot Tub In Chicago, Illinois

Chicago is one of the largest cities in the U.S. and has a famous skyline, punctuated by skyscrapers and striking architecture to see, famous museums to explore and a myriad of holiday activities to experience. Chicago also features numerous hotels with restaurants, gyms, spa services and more. But, there is nothing as welcoming as a soak after a long, weary day of exploring a city. If this is something that appeals to you, there are several hotels in the city to suit your taste and preference, from accommodations with quirky attributes to charming, romantic hotels. Select the best one for you from our list of the best Chicago hotels with hot tubs.
Rent A Boat
Rent A Boat In Chicago, Illinois

The Windy City, Chicago, is one of the most populated and most popular cities in the U.S. With a rich history, beautiful geographic location and a culturally diverse population, Chicago attracts thousands of visitors each year. Museums, award-winning restaurants, craft breweries, bars, nightclubs, parks, sports arenas, shopping outlets, aquariums, art galleries and a ton of other attractions are on offer here. Whether you are in the city to check out The Magnificent Mile, take the Architecture River Cruise or take in panoramic views of the city from SkyDeck Chicago, you need a comfortable place to rest your head at the end of the day. Stay at a unique accommodation in the form of a houseboat and experience life on the water. To know more, check out our suggestions to rent a boat in Chicago, Illinois.
Indian Restaurants
10 Best Indian Restaurants In Downtown Chicago, Illinois

Set on lake Michigan in the stunning state of Illinois, Chicago is a breathtaking metropolis that will captivate you with its dramatic cityscape, high-end attractions, family-friendly recreation area, boutique stores, and exquisite restaurants. In the heart of the city lies downtown Chicago, where business meets leisure. Tourists have lots to do in this bustling place. You can take souvenir pictures in Grant Park and Buckingham Fountain, spend some family time in the fascinating Lincoln Park Zoo, browse through the exhibits in the Museum of Science and Industry, and a lot more. For foodies with a huge appreciation for Indian food, here is a list of the best Indian restaurants in downtown Chicago, Illinois that are worth a try. Feel free to browse below.
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.
Cheap Hotels
Top 13 Budget Hotels In Chicago, Illinois

Chicago is an absolutely amazing city, filled with unique architecture, plenty of tourist attractions, and a vibrant nightlife. Your budget should not prevent you from being able to experience all that Chicago has to offer especially if there's a city hotel with an affordable price. From 4-star hotels in downtown to hotels for families, there are a plethora of great but cheaper accommodations around Chicago. Without further adieu, here are some of the best budget hotels to help you save money during your stay in the city.
Live Music
Live Music In Chicago

Sitting on the shores of Lake Michigan, Chicago is one of the largest cities in the US, blending high-rise buildings, bold architecture, museums, culture, and art. It wouldn’t be a trip to Chicago without a visit to the Millennium Park, dining, and shopping at Navy Pier, or taking some Instagram-worthy photos on the 103rd floor of The Ledge at Skydeck. But, if we think of something that’s truly iconic to Chicago, that's music. From blues and jazz to gospel, hip-hop, and indie, the city has long been the home of music. Here are the best places to enjoy live music in Chicago today.
Festivals
10 Cool Events And Festivals In Chicago, Illinois

Chicago, Illinois is famous all over the world! This is one of the biggest cities in the United States that offers opportunities from employment to parties! Yes, that's right! There's always something special happening in Chicago, literally, many events took place in here from the Battle of Fort Dearborn, Treaty of St. Louis to World Music Festival and celebrity concerts. This is the home of many festive people, so don't be shocked if someone buys you a drink or invites you to dance and sing. As you check out these mindblowing events, keep yourself cozy and comfy at the best Vrbo vacation rentals and top budget hotels in the city. For more juicy information on the hippest festivals in Chicago, check out the list below!
Famous Buildings
15 Famous Buildings In Chicago, Illinois, The USA

Chicago, Illinois is an absolute architectural wonder with a skyline outlined by skyscrapers of all shapes. The city is studded with Michelin-star restaurants, world-class museums, local theatres and whimsical art installations on the streets. The nightlife with its interesting bars, comedy clubs and live music is an experience worth trying out. Essentially, the city has something for every kind of traveller! So as you plan to explore the city, don’t forget to visit a checklist of iconic architectural marvels. Each building is notable and an extraordinary sight to see. Just be sure to choose your retreat from the city's top budget hotels or the best luxury Airbnbs for your accommodation needs. Go ahead, check the most famous buildings in Chicago, Illinois, the USA and enjoy an experience of a lifetime.
Dive Bars
9 Best Dive Bars In Chicago, Illinois

Chicago is one of the largest cities in the US, notorious for its freezing winters and beloved for its hot deep-dish pizzas. It is also famous for its fabulous architecture, from old art deco buildings to modern skyscrapers. One of the best things to do here is to take an architectural river tour and enjoy the unique perspective of the Chicago skyline from the water. Top attractions include Millenium Park, Art Institute of Chicago, Navy Pier, Willis Tower SkyDeck, and Buckingham Fountain. Don't forget to check out the city's eclectic restaurant and bar scene. Have an awesome visit and mingle with friendly locals at the best dive bars in Chicago, Illinois.
What To Buy
What To Buy In Chicago, Illinois

There are lots of reasons to visit Chicago, Illinois: the city is full of museums, sporting venues, iconic buildings, and delicious restaurants. It’s also a city with tons of shopping opportunities. The Magnificent Mile, the northern section of Michigan Avenue and Chicago’s commercial center, has over 460 retailers and three shopping centers. That doesn’t even include all of the shops to be found in Chicago’s other neighborhoods! If just the thought of wandering through all those stores makes you feel tired, here is a list of the top things to buy in Chicago to help you narrow down your shopping goals!
Gluten Free Bakeries
10 Gluten-free Bakeries In Chicago, Illinois

Chicago, Illinois, is a vibrant and lively city, with a variety of craft breweries and distilleries, a rich history, spectacular art and culture, and a diverse and innovative food scene. It’s no longer just steaks and hot dogs, although they do serve some of the best in the country; the Chicago cuisine goes beyond that and can be found in fine dining restaurants, prominent cocktail bars, and some of the finest bakeries. Whether it’s bread, pastries, or cakes, Chicago is home to some finger-licking bakeries and pastry shops. If you want to know where to find the best gluten-free bakeries in Chicago, Illinois, join us on this flavorful journey.

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