Downtown Chicago Vacation Packages

Yes! Save by combining your lodgings and airfares. Expedia has plenty of outstanding Downtown Chicago vacation packages that'll simplify things and give you more money to splurge!

Crafty travelers can save up to $583* by securing a package deal on Expedia.

Our extensive international database lists more than 750,000 properties worldwide and 550 partner airlines. With such a great range of options, organizing your dream vacation will be a breeze!

Not 100% sure about your booking? You won't pay us a cancellation fee if you make changes to almost any reservation.

Preparing for your trip to Downtown Chicago? Keen for a few pointers about what to see when you're there? That's where we can help!

We couldn't envisage a better place to base yourself than Downtown Chicago. World-renowned attractions such as the Art Institute of Chicago and Willis Tower will be just moments away.

A jam-packed day of sightseeing can be tiring business. Fortunately, you won't have to travel far to get to Navy Pier and the Chicago Cultural Center. These nearby wonders will not disappoint!

If you're bored of dining indoors, grab some takeaway and enjoy a revitalizing lunch among the trees at Millennium Park. There's an excellent range of things to keep you busy in this destination. Those without a head for heights might want to look away, but anyone with a passion for skyscrapers shouldn't miss John Hancock Center. Reaching up towards the heavens, it's a stately fixture of the local area's skyline. Still got time to spare? Skydeck Ledge gives sightseers dazzling vistas as well as some impressive photo opportunities.

Life is either an extraordinary adventure or nothing at all, so why not throw yourself into some new and interesting experiences?

Kick off your trip to Downtown Chicago by trying a few of these activities:

• Chicago Mob Tour: Criminals & Gangsters Bus Tour
• 1893 World's Fair Walking Tour with Bars
• Vacation Photographer in Chicago
• Bikes, Bites & Brews - West Side Foodie Ride
• Spirit of Chicago Lunch Cruise
• Chicago Favorites - Food Tasting Walking Tour

If you'd rather take a look at a full list of activities, jump onto our Downtown Chicago things to do page.

Whatever kind of accommodations you're searching for, Downtown Chicago has you sorted. With 122 listed options to pick between, you'll be sure to find one that's perfect for your cheap vacation or luxury getaway.

If you're looking to save a few pennies, there are some excellent low-cost properties here, such as the Trump International Hotel & Tower Chicago (401 N Wabash Ave) and The St. Clair Hotel (162 East Ontario Street). When only the finest things in life will do, sleep in style at the Chicago Premier Suites (540 N State Street) or The Peninsula Chicago (108 East Superior Street). These luxurious retreats are also nearby.

Is being near the Art Institute of Chicago your chief priority? The Langham, Chicago and the JW Marriott Chicago are both within strolling distance.

Getting on a plane to Midway International Airport (MDW)? It's situated 9 miles to the southwest of the middle of this neighborhood. Time to claim those bags and get your trip to Downtown Chicago rolling!