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Lakefront Hotels
5 Best Lakefront Hotels In Chicago, Illinois - Updated 2025

Chicago is best known for its signature deep-dish pizza and the iconic art installation, Cloud Gate, also known as The Bean. However, it has plenty more attractions and dining options to explore. Jumpstart your Chicago food trip by visiting Uno Pizzeria and Grill, the restaurant said to be the birthplace of deep-dish pizza. Then, explore other Chicago classics, such as hotdogs at The Wiener Circle in Lincoln Park. Since the city is also known as a craft beer capital, be sure to visit breweries, such as Goose Island and Half Acre. Music is an important part of the city, and you will see many jazz clubs such as GreenMill Jazz Club here. The city also prides itself on having great waterfront views at Lakefront Trail. Get to experience all that Chicago has to offer. Start off by scroll down to see the best lakefront hotels in Chicago, Illinois.
Hotels With Free Parking
3 Best Hotels With Free Parking In Downtown Chicago, Illinois

The Chicago skyline is one of the most recognizable in the US, and the downtown area is the beating heart of the city. Made up of seven neighborhoods, Chicago's downtown consists of The Loop, West Loop, South Loop, River North, Gold Coast, Streeterville, and Lakeshore East. You'll find skyscrapers, business headquarters, and major shopping spots, but that's not all. Places like Grant Park in The Loop host yearly summer festivals and Oak Street Beach in North Lake Shore Drive is a popular summer spot for soaking up the sun. The museums along Magnificent Mile are popular attractions in the cold winter, along with the myriad of restaurants to try nearby. Parking can be a hassle anywhere in the city, especially downtown. So if you're visiting, check out these best hotels with free parking in Downtown Chicago, Illinois.
Hotels With Kitchen
10 Best Hotels With In-Room Kitchen In Downtown Chicago

Whether you're considering going away for a weekend or several days, Chicago has all the offerings of a major city, with nightlife venues, shopping districts, and world-class museums. Check out Millennium Park with its Cloud Gate and Crown Fountain that attracts many visitors. If you are a shopaholic, Magnificent Mile is the place to be. Carry your credit card as you will spend much in the luxury retailers and department stores found in this magnificent shopping area. Visit Lincoln Park Zoo and encounter its resident hippos, sloths, gorillas, and zebras. For an overview of the city, go on an exciting Chicago River Cruise where you will enjoy fabulous views of the city’s skyscrapers. If you'd rather cook for yourself on your vacation, this list of the best hotels with in-room kitchen in downtown Chicago, will surely help.
Spa Resorts
12 Best Spa Resorts In Chicago, Illinois

Chicago, located in Illinois on the shores of Lake Michigan, is one of the major cities in America. The 1,451-foot (442.3- meter) Willis Tower (originally the Sears Tower) and the neo-Gothic Tribune Tower are among the city's many famous skyscrapers. Chicago boasts everything a great metropolis should have: excellent museums, exciting retail areas, and places to party into the early hours. You should spend a lot of time around Grant Park if you are here to study. Start your trip with a boat tour of the architectural landmarks along the Chicago River or Lake Michigan. The Windy City is also home to many Airbnb vacation rentals, resorts, and 5-star hotels, several of which have award-winning spas. If you require some relaxation in the form of a luxurious massage, facial, or treatment, go no further than these best spa resorts in Chicago, Illinois.
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:
Eco Hotels
10 Green Hotels In Chicago, Illinois

Chicago is popularly referred to as the “Windy City”. This world-class city gets its peculiar nickname from the relaxing breeze blowing through the city from Lake Michigan – which it sits on. This incredible city has changed, over the years, from a small trading route to a significant multi-commercial and industrial hub in the country. A place of diverse people and cultural heritage, Chicago doesn’t just have thriving businesses and companies; the city is very well blessed with aesthetic beauty. With beautiful extensive parklands, fantastic architecture, captivating museums and monuments, Chicago attract millions of tourists every year. The city also believes in environmental sustainability and has put in several efforts to make Chicago eco-safe. So if you are visiting the great city in the heart of America, you don’t have to give up your comfort and luxury to stay eco-friendly. Here is a list of green hotels in Chicago, Illinois for you to stay in:
Jazz Bars
9 Best Jazz Bars In Chicago, Illinois

Chicago is a beautiful city seating on the shores of Lake Michigan in Illinois. With its skyline pierced by tall skyscrapers such as the John Hancock Center and spectacular ground level architecture such as the mired bean sculpture at the Cloud Gate, Chicago has more to offer than meets the eye. Other such sites include the Willis Tower, a spectacular skyscraper boasting city vistas, the Navy Pier, an amazing destination with shops, food and rides, and the famous Millennium Park, a green space with a theater, art and ice rink. Take a look at our article on the top 10 most recommended jazz bars in Chicago, Illinois.
Casual Restaurants In
10 Casual Restaurants In Chicago, Illinois

It's best to pack clothing a size bigger than yours for your travel to the Windy City - for Chicago is an absolute chowhounds delight! While the city is where numerous regional specialities such as the Chicago-style hot dog and the lip-smacking deep-dish pizza originated, it is also a place where you can find food from the Deep South and some delectable Macanese fare too. Whether you're breakfasting, lunching, brunching, dining, or just snacking, Chicago has dime a dozen restaurants to suit every craving for every time of the day. Here's presenting a list of the best casual restaurants in Chicago, Illinois.
Halal Restaurants
10 Best Halal Restaurants In Chicago, Illinois

The Windy City is a city steeped in history, with a thriving cultural scene. As the third-most populated city in the US, it's a diverse melting pot of different cultures. Its variety is well-represented in its plethora of food choices - from the quintessential Chicagoan deep-dish pizza and the perennial crowd favorite, the Italian beef sandwich to the vibrantly-colored rainbow cones. No matter your dietary restrictions, there's something for everyone here in Chicago. If you're finding it difficult to find halal restaurants near you in the city, don't worry - here's a list of the 10 best halal restaurants that'll blow your socks off in the Windy City.
Food Markets
10 Food Markets In Chicago, Illinois

Chicago is a city that has everything. From great museums to beautiful parks, there is something here for everyone. But even with so many good restaurants and plenty of grocery stores spread out across the city, sometimes you just want the fresh food that a food market can offer. These top 10 food markets are some of the best that Chicago has to offer. With plenty of local produce, you can do your fruit and veggie shopping with ease. Additionally, there are great snacks and pastries or options for a quick lunch or breakfast. Many of these markets also have a focus on educating the community. Check out the best food markets in Chicago, Illinois. Take a look to see what interests you most, and enjoy.
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
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.
Hotels With Pools
Top 16 Chicago Hotels With Pools

Chicago, the Windy City is the biggest city in Illinois. It is known for former President Barack Obama and the Chicago Bulls of the GOAT Michael Jordan. It is one of the most important cities in the whole United States, with tons of history, great economic power, and of course, a lot of top attractions. Although Chicago is at the edge of the Great Lakes and has a river run through the city, how perfect would it be for you to book a room in a hotel that has its own swimming pool? Our team of experts here in Trip101 made a thorough search and offers you diverse options of Chicago hotels with pools for a memorable and luxurious stay. Do I hear the splash already?
Romantic Staycations
14 Best Romantic Staycations In Chicago, Illinois

Chicago is one of the top destinations in North America when it comes to both business and pleasure. Couples looking for a romantic getaway will be happy to find an almost endless list of possibilities in the Windy City. You could wander around Lake Michigan’s shoreline, explore the many gourmet options and Viator tours, or check out the Magnificent Mile. If you’re looking to surprise your partner with a romantic gesture, you could try taking a carriage tour of Michigan Avenue, hop on the Navy Pier Ferris Wheel, or head over to 360 Chicago, for breathtaking city views. There are also countless restaurants with a view where you can treat your partner. If you want to take a break from all the outdoor activities, stay in your hotel room and relax with a spa massage, have a drink on the rooftop bar, or check out the pool, read on, as we’re about to show you the best romantic staycations in Chicago, Illinois.
Rv Rentals
13 Best RV Rentals In And Near Chicago, Illinois, To Book Now

Jazz music, Polish sausages, deep-dish pizzas, glass and steel skyscrapers, Chicago-style hot dogs - Al Capone's beloved Chicago is unostentatiously extraordinary. The Windy City also has tons to offer adventurers, outdoor enthusiasts, road trippers - basically anybody who's looking to get out and experience the natural beauty of the region, whether you want to head to the lovely green forests or simply drive down America's highways. What better way to do so than to avoid campsites and instead hit the road in campers, travel trailers, or motorhomes? Explore the Windy City, its many cool events and festivals, and the surrounding region by renting an incredible RV. Check out our list of the best RV rentals in and near Chicago, Illinois, to book now. https://www.youtube.com/watch?v=a78Tds77ApQ&autoplay=1
Hotels In
11 Best Hotels in River North, Chicago - Updated 2025

If you're into design and arts, you should definitely explore River North. When you take a walk around the area, your eyes will surely marvel at the various art galleries and studios. River North is popularly known as the gallery district and despite modern changes through the years, it has maintained its reputation as one of the top destinations for art galleries in Chicago. Moreover, the area is highly recommended to travelers who love grooving into the nightlife. Hop on to Hubbard Street and Franklin Street where you'll find numerous dance clubs, entertainment hubs, and restaurants. The party scenes in the lively rooftop bars in River North are also worth checking out. Before you get excited about what the area has to offer, of course, plan where to spend your nights. We've curated the best hotels in River North, Chicago so make sure to read until the end!
Things To Do Alone
12 Things To Do Alone In Chicago

Sitting on Lake Michigan, Chicago is a city that not only boasts of its position to this stunning lake but it also prides itself on being one of the largest cities in the US boasting many hotels with lake views. Experience luxury and convenience at hotels in downtown Chicago with stunning skyline views, and easy access to top solo activities in Chicago. Known locally as the Windy City, Chicago is an eclectic destination that is punctuated by a love for music and the arts. This city has managed to shake off a dark past of crime, transforming this history into a thrilling tale. Stories of gangsters like Al Capone have reverberated across the world and Chicago started it all. This fascinating city has a lot to offer. If you’re travelling alone, check out the top things to do alone in Chicago and make the most of your solo adventure.

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