Downtown Chicago Vacation Packages

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Top Holiday Package Deals in Downtown Chicago

Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago

Downtown Chicago

CA $1,114

per person

Oct 21 - Oct 24

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9.4/10 Exceptional! (5,106 reviews)

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,312

per person

Nov 9 - Nov 12

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.6/10 Exceptional! (2,003 reviews)

Freehand Chicago

Downtown Chicago

CA $1,759

per person

Oct 8 - Oct 12

found 16 hours ago

Roundtrip flight included

Montreal (YMQ) to Chicago (ORD)

7.8/10 Good! (3,367 reviews)

The Talbott, Autograph Collection

Downtown Chicago

CA $1,153

per person

Oct 21 - Oct 24

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9.4/10 Exceptional! (165 reviews)

Cute hotel in great location..make sure to ask for a street side room or your view will be a brick wall and the room will be like a dark cave. 😭

Reviewed on Sep 4, 2026

The Emily Hotel

Downtown Chicago

CA $1,304

per person

Oct 21 - Oct 24

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9.2/10 Wonderful! (1,351 reviews)

Where to stay in Downtown Chicago

Find the best Downtown Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Chicago

A river with yellow boats, a bridge, and tall buildings.

The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

A wooden pavilion with a view of a city skyline and a body of water.

Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

A nighttime cityscape with fireworks over a body of water, a Ferris wheel, and illuminated buildings.

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line).

Downtown Chicago Hotel Deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

CA $158

CA $188 total

Sep 7 - Sep 8

includes taxes & fees

8/10 Very good! (10,271 reviews)

"Very nice and helpful staff. Close to many downtown amenities"

Reviewed on Sep 4, 2026

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

CA $198

CA $235 total

Sep 8 - Sep 9

includes taxes & fees

Kasa Magnificent Mile Chicago

One Superior Place Chicago IL

9.4/10 Exceptional! (888 reviews)

"We thoroughly enjoyed our stay at Kasa- check in instructions were clear and hassle free. The unit was spacious and clean, with a terrific view. Highly recommended!"

Reviewed on Sep 4, 2026

Get rates

See all 1,606 properties in Downtown Chicago

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does a Downtown Chicago vacation package cost?

Go from looking to booking with our Downtown Chicago vacation packages, which start from just CA $1,114. Handpick the hotels and flights that suit your travel style. Then, add on a couple of tours or activities for an amazing adventure.

How do I get a cheap travel package to Downtown Chicago?

Bundle your bookings with Expedia to save big on your next trip. With more than 550 partner airlines and 1,000,000 hotels across the world, your Downtown Chicago vacation package can be tailored exactly to suit your budget. With all that extra money, why not include one or two fun tours and activities? It's an easy way to unlock even more savings. The vacation you've always dreamed of in Downtown Chicago is much closer than you thought!

How far in advance should I book my Downtown Chicago vacation?

While not all airlines advertise tickets early, you can normally look up international airfares on Expedia up to 12 months in advance. This is the time you'll score some incredible deals. If you've left things to the last minute, you could still be in luck. Discounted prices occasionally emerge a few weeks before departure.

What does an Expedia Downtown Chicago travel package include?

Packages include flights, hotels and rental cars, but you can mix and match them to create your ideal Downtown Chicago trip. You can also add on fun things like activities and tours once you've made your booking. You're in charge! When you combine your bookings with Expedia, you'll score discounts you won't find elsewhere.

What should I know before booking a Downtown Chicago travel package?

Our prices are always low. However, you'll pick up even better deals if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and tons of choice.

Can I choose my airline with a Downtown Chicago Expedia vacation package?

Yes — that's the beauty of an Expedia vacation package. You're in charge! We have more than 550 partner airlines throughout the world, so you have lots of choice when arranging your Downtown Chicago trip.

If I'm not able to travel, can I cancel my Downtown Chicago vacation package?

You can. We understand that even the best-laid plans can go awry, so we're happy to help if you have to make changes to your Downtown Chicago vacation package. You may be able to change or cancel your itinerary for free if you've booked in the last 24 hours. Your airline, hotel or car rental company may impose a fee if your booking was made more than 24 hours ago. Have a look at our Customer Service Portal for further information. Also, be sure to check your itinerary for the finer details on change fees.

Stay near popular Downtown Chicago attractions

A Ferris wheel and a carousel at a fairground.

Navy Pier

9.0/10 (24,140 reviews)

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

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A cityscape with modern skyscrapers and the Cloud Gate sculpture.

Millennium Park

9.4/10 (30,446 reviews)

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

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A river with boats, surrounded by tall buildings and a clear sky.

Chicago Riverwalk

9.6/10 (13,574 reviews)

Stroll along the waterfront of the Chicago River to pass some of the city’s most appealing attractions and appreciate how a once grim area has been successfully revamped.

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A busy urban street with a train crossing, tall buildings, and a tram.

Michigan Avenue

9.4/10 (15,813 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

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