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7800 Travelers rated Chicago highly for Urban and Skyscrapers

Due to coronavirus (COVID-19) travel advisories, some destinations may be unavailable for certain dates. Find out more.
Due to coronavirus (COVID-19) travel advisories, some destinations may be unavailable for certain dates. Find out more.
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Book a package and join the 188 others who’ve received 100% off their flights this year!

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Chicago Vacation Package Deals

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.

Chicago Travel Guide

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.

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.

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

LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by Hilton
4.5 out of 5.0 85 East Wacker Drive, Chicago, IL
Free Cancellation
$109
4.4/5 (94 reviews)

The beautiful room and it’s view were our favorite things about the hotel. The dinner at Ocean Prime was delicious.

Reviewed on Jul 18, 2020
Guests of LondonHouse Chicago, Curio Collection by Hilton enjoy features like a full-service spa, free WiFi in public areas, and 13 meeting rooms. The front ...
Sofitel Chicago Magnificent Mile
Sofitel Chicago Magnificent Mile
4.5 out of 5.0 20 E Chestnut St, Chicago, IL
Free Cancellation
$143
4.6/5 (66 reviews)

The hotel was nice and the staff was very pleasant. My husband and I were in walking distance from the John Hancock building and anything else was either in walking distance or we took the Red L train to everything else. The McDonalds around the corner had the best burgers and fries we ever tasted. ...

Reviewed on Jul 7, 2020
Renovated in 2018, Sofitel Chicago Magnificent Mile offers a 24-hour fitness center, free WiFi in public areas, and a 24-hour business center. Valet parking ...
Best Western Grant Park Hotel
Best Western Grant Park Hotel
2.5 out of 5.0 1100 S Michigan Ave, Chicago, IL
Free Cancellation
$64
4.1/5 (149 reviews)

It’s good and price was very fair . Not far from the main city of Chicago

Reviewed on Jul 30, 2020
Guests of Best Western Grant Park Hotel enjoy a fitness center, free WiFi in public areas, and a business center. Valet parking is available for USD 52.00 per ...

Things To Do during your Chicago Vacation

See all 149 things to do in Chicago

^Savings based on all package bookings with Flight + Hotel made on Orbitz.com from January 1, 2019 to December 31, 2019 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.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.