Chicago Vacations

Are you searching for awesome Chicago prices? Save time by letting the team at Orbitz bundle up your flights and hotels.

You have the opportunity to save up to $536* when you bundle up! All you have to do is pick your preferred airfares, hotels, experiences and rental cars.

And remember — you'll be able to tailor your vacation by selecting from 500 partner airlines and no less than 500,000 worldwide hotels. You have the freedom to choose exactly what you want!

There are infinite room types, flight options and breathtaking experiences to satisfy your wandering spirit. Which ones will you pick?

Join Orbitz Rewards

Rewards programs are a dime a dozen. But what would life be like without those perks and bonus savings? We've developed a simple program that will reward you quick! To gain instant Orbucks, just keep booking with us!

Also, just book four nights for gold membership and 12 nights for platinum membership. So, what does that get you? Well, you'll have special perks, like complimentary breakfast, Wi-Fi and more, at Orbitz Rewards VIP Hotels. And how do you redeem your Orbucks? Simple — use your Orbitz Rewards points on your following booking.

Chicago Travel Guide

Where is Chicago?

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

So, what's the first stop? You'd be nuts to leave out the Art Institute of Chicago and Willis Tower. While you're checking out iconic attractions, why not take a look at the McCormick Place and the University of Illinois Chicago too?

Navy Pier and the Lincoln Park Zoo are just a few of the interesting attractions in the area. These aren't for you? Don't fret — you're flush with choice here. Other fine options are Lincoln Park and the Chicago Cultural Center.

An essential part of the local infrastructure, Millennium Park provides residents and visitors with a green space for relaxation and recreation. Enjoy a walk or take off your shoes and feel the lush grass beneath your feet. Want to keep the good times rolling? Look up at the skyline and appreciate John Hancock Center, one of the most impressive buildings. See if it's possible to climb to the top and watch the world go by from way above. But wait, that's not all! If you're looking to get your bearings, be sure to make the trip up to Skydeck Ledge. Not only will you be privy to panoramic views of the area, it also makes for the perfect place to snap a selfie or two.

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.

*Savings based on all holiday package bookings with Flight + Hotel on Orbitz.com from July 1, 2015 to June 30, 2016, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.

^The travel product supplier may, however, charge cancellation fees which you will be required to pay. Terms and conditions apply.