Chicago Hotels

Find the best deals in Chicago

With a massive choice from some of the best hotels, Enjoy the best way to find the best prices for hotels in Chicago.

• Huge choice of hotels to suit every budget
• Save by booking early compared to buying on the day
• 15 years travel experience

Cheap hotels in Chicago

Chicago is one of the USA’s most tourist-abundant cities, with its Lake Michigan shoreline and vibrant, bustling streets forming the base of its international appeal. But, deep-dish pizza and historical landmarks aside, Chicago is also home to thousands of accommodation options to suit the needs and preferences of every guest. No matter what neighborhood of Chicago you are visiting, Enjoy Travel has some great deals on hotels to suit your preferences.

No matter your reason for visiting Chicago, whether for business or leisure, Enjoy Travel is your helping hand for finding the best deals on hotels and accommodation options in the city, and across the world. With thousands of hotels to choose from, browse Enjoy Travel to guarantee your chances of securing your favorite vacation accommodation.

Enjoy Travel is your ultimate guide for all things travel accommodation-related. Using our hotel comparison platform, you can compare prices on thousands of hotels in the Chicago area, and find your perfect one in mere minutes. With the help of our comparison platform’s toggle tools and filters, you can narrow down your search until you find the hotel of your dreams.

How to Find the Best Chicago Hotel Deals

Chicago’s bustling streets and abundance of things to do may leave you a little overwhelmed and unsure of where best to stay. If you’re unsure of how to find the best deals and offers on hotels, look no further than our helpful tips and advice:

Cast the net wide: While hotels may be the preferred accommodation option, as everything you need is provided for you, hotels are also extremely popular with tourists. This means that the hotel you’ve had your heart set on could sell out or increase its rates the closer it gets to your vacation. In this case, have some backup accommodation options available, such as vacation rentals or B&BS, which may work out to be cheaper.

Book in advance: Chicago is usually busy all year round, which emphasizes the importance of staying organized and booking your hotel in advance of peak tourist seasons. Try to book around 2-3 months in advance of your vacation date to be in with the best chance of securing your favorite hotel.

Rely on travel platforms: Travel platforms like Enjoy Travel can help you find the best deals on hotels in minutes. You can also filter your searches to align with your own preferences, whether based on amenities, location or price of your hotel.

Discover Chicago Secrets and Surprises

Within every city, there are the attractions that give the city its reputation and that are loved by both locals and tourists alike; then there are the lesser-known and often secret places that may only be known to locals or people who have done a lot of research about their chosen city. Chicago is full of secret and hidden places that, once discovered, will make your trip memorable and more exciting. Take a look at these Chicago hidden gems that you should definitely add to your trip itinerary:

Oz Park: Perhaps initially lesser-known to tourists or visitors, Oz Park is located in the North Side of Chicago and brings a touch of fantasy to the city, with its featured statues of well-known movie ‘The Wizard of Oz’ characters. The park is also dog-friendly, so is a great place to wander around with the whole family.

The Drifter Speakeasy: Located underneath the Green Door Tavern, this speakeasy serves cocktails and provides live entertainment to its attendees and those of us who are lucky enough to know how to locate this secret bar.

Dining out in Chicago

Known for its vibrant culinary scene that includes deep-dish Chicago-style pizzas and hot dogs, you’ll be spoilt for choice when deciding on where to eat in Chicago. From fine dining spots and bistros/grills to diners and beloved street food stalls, where do you start? You’d be crazy not to sample some iconic Chicago pizza while you’re there too.

Drinks and nightlife

Chicago is rife with bars, clubs and entertainment venues to give you the best night out you’ve ever had. From quaint cocktail bars and lounges, to dive bars and speakeasies, the choice is yours on how to spend your night. Popular drinks of choice include beers, wines, cocktails like Old Fashioned, and liquors like rum, gin and whiskey.

Must-see sights (what not to miss!)

Chicago is home to many notable landmarks, historical sites and attractions which we’re sure you’ve already added to your list, but to give you as many options as possible, here’s a list of our top suggestions on where best to spend your time in the Windy City.

● Lincoln Park Zoo: Free to enter, this large zoo is one of America’s oldest, and provides many interesting and insightful enclosures and events to keep the whole family happy and entertained.

● Garfield Park Conservatory: One of the largest indoor gardens in the country, this beautiful botanical garden showcases plants from around the world across its acres of land. The conservatory also hosts a lagoon for fishing and a swimming pool. To access the conservatory, you must make a reservation.

● Millennium Park: Made notable for its towering ‘Cloud Gate’ sculpture, Millennium Park is open for public access, and hosts an abundance of fun activities and sights, such as an ice rink and theater, among others.

● Art Institute: A large art museum located in Grant Park, this popular tourist attraction showcases collections of art from across the world and throughout history. This is definitely a must-see attraction when wandering through Chicago.

How to choose the perfect Chicago hotel for your stay

The sheer amount of hotels in Chicago can make it difficult for you to find the perfect one, but Enjoy Travel is here to help take the burden off you. Gone are the days of scrolling through hundreds of hotels and researching where to find the best deals– we will find them for you. Using our hotel comparison platform, you can compare prices on thousands of hotels across Chicago and the US.

Our service helps to put the joy back into planning for vacation, making your accommodation search as hassle-free and stress-free as possible. From North Side to South Side, begin your search for Chicago hotels today with Enjoy Travel.

How to choose the cheapest Chicago Hotel for your stay

Finding the best deals on hotels has never been easier! Cheaper hotels don’t have to compromise on quality, and the hotels we source are comfortable, convenient and high-quality. But, if you’re wondering how to improve your chances of staying somewhere that doesn’t break the bank, here are our helpful tips:

● Book in advance: Booking in advance is a good idea in heavily-populated cities and tourist hubs to book your hotel months in advance of the date you intend to travel. The closer your vacation dates get, the more likely it’ll be that hotel prices will increase as they become more in demand. Try to book around 90 days in advance to keep your hotel prices low.

● Have backup options: Having cheaper accommodation options as backup options in the case of your hotel being sold out or expensive is a good idea. While they may not be your first choice, these types of accommodation will provide you with the same level of comfort and convenience as hotels would.

● Compare prices with Enjoy Travel!