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Book Chicago Vacations

Save up to $374^ on your trip when booking flight + hotel together

Trip deals to Chicago for 2021

Conrad Chicago
The Langham, Chicago
The Peninsula Chicago
Courtyard by Marriott Chicago Lincolnshire
Courtyard by Marriott Chicago Magnificent Mile

Chicago Travel Guide

Let the travel experts at Orbitz find the best-value flight and hotel packages for you. If you're looking to design your perfect Chicago trip, you're on the right track! You have the chance to save up to $369^ if you combine your bookings. All you've got to do is pick your desired hotels, rental cars, airfares and experiences. And we're not finished! With 500,000 worldwide hotels on our system and 500 airline partners, you'll have stacks of freedom to make your getaway uniquely yours. There are limitless options to suit your distinct style. All you have to do is pick your package and get set for a stunning vacation.

Where is Chicago?

Sometimes it's great to travel without a plan, but even the most spontaneous travelers ought to have a basic understanding of where Chicago is. It is about 180 miles northeast of Illinois' capital, Springfield. Chicago is also 19 miles northwest of East Chicago. With plenty of things to do in this area of Illinois, it's easy to understand why 2,700,000 people reside here.

Places to Visit in Chicago

Drawing crowds of sightseers from all corners of the world, the Art Institute of Chicago and Willis Tower should be at the top of your to-do list. This place is bursting at the seams with top-notch sights. After that, make your way to the McCormick Place and the University of Illinois Chicago. Chicago is home to loads of worthwhile tourist attractions, such as Navy Pier and the Lincoln Park Zoo. Prefer to go somewhere else? It won't be a problem — you'll have plenty of choice here. A few other options include Lincoln Park and the Chicago Cultural Center. Crisp air and green surroundings are found in abundance at Millennium Park. Want to keep the good times rolling? Sleek, shiny and gigantic, skyscrapers like John Hancock Center are sights to behold. Be sure to stop, tilt your head back and admire this imposing monolith! But wait, there's more! To get a sweeping view of the surrounding area, head on up to Skydeck Ledge.

Car Rentals in Chicago

Take your travel lust further by checking out car rentals in Chicago. It doesn't matter where you go or what you're wanting to do, Orbitz will help you find a rental that satisfies your adventurous spirit. You can go right from the plane to the car at Midway International Airport. Budget and Avis are both a short distance from arrivals. Consider renting a car from Enterprise at 20 E Randolph St 3Rd Fl. They're right in the heart of the city. If there isn't anything to your taste there, Budget at 214 N Clark St is your next best bet.

Where to stay in Chicago – Hotel Accommodation

Book a place to stay and get ready for your big adventure! Orbitz offers as many as 165 hotels in Chicago. The Waldorf Astoria Chicago is a brilliant choice if you're searching for top-end accommodations. If that's fully booked, check out The Peninsula Chicago. On the other hand, check out the amenities at the Old Chicago Inn or the Urban Holiday Lofts if you're traveling on a stricter budget. The Langham, Chicago is only 0.6 miles away if you're keen to stay close to the Art Institute of Chicago. Located 0.5 miles away, the JW Marriott Chicago is practically on the doorstep too!

Nearest Airports to Chicago

After traveling all the way to Midway International Airport (MDW), you'll just have one more journey to take before you reach your final destination. The terminal is located 9 miles southwest of the downtown area.

Popular Places to Visit Near Chicago

Once you've spent some time seeing the best of Chicago, world-renowned attractions are on offer right around the corner! Six Flags Great America draws visitors from all nations. North Chicago, about 35 miles from Chicago, is a convenient base when stopping by this unmissable attraction.

No Cancellation Fees

Canceling or making changes to a booking can often be tricky — but not with us! We don't charge a fee, which will make it a piece of cake.^ Airlines and hotels can have the same policy, so contact them to find out.

Top rated hotels for your Chicago vacation

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Top things to do in Chicago

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