Downtown Chicago Vacation Packages: Bundle & Save up to $C634 in 2019

Save Time and Money with Downtown Chicago Vacation Packages

Have you considered booking a Downtown Chicago vacation package? It's simple with Expedia, and you'll be able to buy a few nice dinners or souvenirs for your buddies back home with the cash you save.

Would you like to save up to C$590*? Book your family's package deal on Expedia today!

With more than 400 partner airlines and 321,000 worldwide properties, our global database can get you to your ideal vacation spot.

Almost all accommodations can be cancelled with no hidden fees from us.

Places to Visit in Downtown Chicago

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.

Popular Activities for your Downtown Chicago Vacation

It's no secret that you don't take time off work to sit in a cramped plane seat and sleep in a different bed. Traveling is all about the exciting adventures you have while you're away!

Jump-start your trip to Downtown Chicago by trying a few of these activities:

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

Downtown Chicago Accommodations

After a long day of activities, you'll be in need of a comfy bed. Fortunately, there's a wide range of accommodations in Downtown Chicago. Decide between as many as 122 options and kick off your luxury getaway or cheap vacation.

Thinking about where to spend your evenings? Just remember — cheap doesn't have to mean bed bugs and old-fashioned linen! You'll find clean, budget options such as the Trump International Hotel & Tower Chicago (401 N Wabash Ave) and The St. Clair Hotel (162 East Ontario Street). If Champagne and caviar are more to your liking, grab your designer luggage and head towards the Chicago Premier Suites (540 N State Street) or The Peninsula Chicago (108 East Superior Street).

Downtown Chicago provides some excellent options for those wanting to stay in the vicinity of the Art Institute of Chicago. Both The Langham, Chicago and the JW Marriott Chicago are within an easy walk of this unmissable attraction.

Nearest Airports to Downtown Chicago

Let's be honest, no one loves wasting time at the airport. However, when you imagine the amazing trip to Downtown Chicago ahead of you, it becomes less of a chore. After all, you'll be only 9 miles (14 km) to the southwest of the neighborhood center when the plane comes in to land at Midway International Airport (MDW).

*Savings based on all vacation package bookings with Flight + Hotel on Expedia.com from January through December 2017, as compared to 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.

*Savings based on all vacation package bookings with Flight + Hotel on Expedia.ca from January through December 2017, as compared to 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.

Guide to Exploring Downtown Chicago

Art Institute Of Chicago

Explore a massive collection of works celebrating different cultures and historical times, from ancient Egypt to modern installations.

See hotels near here

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

See hotels near here

Millennium Park

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

See hotels near here

Willis Tower

Visit the Skydeck and gaze down over the Chicago cityscape from a dazzling 1,353 feet above the sidewalk.

See hotels near here

Chicago Theatre

See a stage show at this iconic cultural beacon, which still captures all the splendor of a trip to the movie theater in the early 20th century.

See hotels near here

Water Tower Place

Enjoy endless shopping, see exhibits of sporting memorabilia and attend shows at a live theater at this huge shopping mall.

See hotels near here

Buckingham Fountain

This enormous art deco installation gives free regular water and light shows symbolizing the power and might of Lake Michigan.

See hotels near here

Pritzker Pavilion

Free concerts and Frank Gehry’s characteristic forms are some of the attractions of this modern performance venue in Chicago’s Millennium Park.

See hotels near here

Crown Fountain

Innovative and certainly unique, this art installation in Millennium Park features the faces of 1,000 Chicagoans blown up five stories tall.

See hotels near here

Grant Park

Chicago’s front yardis a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

See hotels near here

Rookery

Built by famed 19th-century architects and renovated in 1907 by Frank Lloyd Wright, this early skyscraper is a great stop on a Chicago architecture tour.

See hotels near here

Top Hotel Deals

See all 306 properties in Downtown Chicago

Palmer House a Hilton Hotel C$135

See details

Palmer House a Hilton Hotel

17 E Monroe St, Chicago, IL

4.2

of 5, from 11,634 reviews

4.0 out of 5.0

This 1925 Beaux Arts-style Chicago hotel is steps from Millennium Park, 2 blocks from Macy's and the Art Institute, and 1 mile from Lake Michigan, Magnificent Mile shopping, and Wrigley Tower.

Hyatt Regency Chicago C$160

See details

Hyatt Regency Chicago

151 East Wacker Dr, Chicago, IL

4.4

of 5, from 10,490 reviews

4.0 out of 5.0

This Magnificent Mile hotel is located among Chicago's world-class shopping, restaurants and attractions. The Navy Pier, Millennium Park and Art Institute are less than a mile away.

Embassy Suites Chicago Downtown Magnificent Mile C$158

See details

Embassy Suites Chicago Downtown Magnificent Mile

511 North Columbus Drive, Chicago, IL

4.4

of 5, from 5,913 reviews

4.0 out of 5.0

The Embassy Suites Chicago Downtown Magnificent Mile offers a newly renovated fresh look and is located two blocks from Navy Pier, Magnificent Mile shopping, and within walking distance to Millennium Park.

Freehand Chicago C$93

See details

Freehand Chicago

19 East Ohio Street, Chicago, IL

4.2

of 5, from 2,159 reviews

3.5 out of 5.0

Located in River North, this hotel is within a 10-minute walk of Chinese Consulate, Holy Name Cathedral, and Northwestern Memorial Hospital. Museum of Contemporary Art and Water Tower Place are also within 15 minutes. Grand Station (Red Line) is only a 2-minute walk and Chicago Station (Red Line) is 7 minutes.

The St. Clair Hotel – Magnificent Mile C$93

See details

The St. Clair Hotel – Magnificent Mile

162 East Ontario Street, Chicago, IL

4.1

of 5, from 223 reviews

2.5 out of 5.0

The hotel is a half-block from the Magnificent Mile and an 8-minute walk from Grand/State Metro Station. Many attractions are within a 15-minute walk, including the Wrigley Building and Navy Pier, where guests can hop on a boat cruise to see the city's famous skyscrapers from the water.

Congress Plaza Hotel C$117

See details

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

3.6

of 5, from 4,148 reviews

3.5 out of 5.0

Built in 1893, this downtown Chicago hotel offers a convenient location across from Grant Park and close to Lake Michigan.

Hyatt Centric Chicago Magnificent Mile C$181

See details

Hyatt Centric Chicago Magnificent Mile

633 N Saint Clair St, Chicago, IL

4.5

of 5, from 2,689 reviews

4.0 out of 5.0

This smoke-free 17-story hotel is 1 block from North Michigan Avenue's boutique and specialty stores, 3 blocks from Lake Michigan, 6 blocks from the State & Grand subway station (Red Line), and 7 blocks from the Navy Pier entertainment center.