Downtown Chicago Holidays & Package Deals

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Top Holiday Package Deals in Downtown Chicago

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

The Talbott, Autograph Collection

Downtown Chicago

NZ$1,333

per person

24 Nov - 29 Nov

found 1 day ago

Return flight included

Pittsburgh (PIT) to Chicago (ORD)

9.4/10 Exceptional! (165 reviews)

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

NZ$1,540

per person

24 Nov - 29 Nov

found 1 day ago

Return flight included

Pittsburgh (PIT) to Chicago (ORD)

9.4/10 Exceptional! (5,174 reviews)

Great location. Clean rooms and common areas.

Reviewed on 17 Sept 2026

The Emily Hotel

Downtown Chicago

NZ$1,365

per person

24 Nov - 29 Nov

found 1 day ago

Return flight included

Pittsburgh (PIT) to Chicago (ORD)

9.2/10 Wonderful! (1,338 reviews)

The staff was super helpful and the room was clean and beautiful!

Reviewed on 16 Sept 2026

Kimpton Gray Hotel by IHG

Downtown Chicago

NZ$1,408

per person

24 Nov - 29 Nov

found 1 day ago

Return flight included

Pittsburgh (PIT) to Chicago (ORD)

9.4/10 Exceptional! (1,010 reviews)

Silversmith Hotel Chicago Downtown

Downtown Chicago

NZ$1,472

per person

24 Nov - 29 Nov

found 1 day ago

Return flight included

Pittsburgh (PIT) to Chicago (ORD)

9.2/10 Wonderful! (2,381 reviews)

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

Magnificent Mile

An avenue brimming with superb shops and restaurants, the Magnificent Mile more than lives up to its name.

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

The Loop

Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

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

River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

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

Lincoln Park

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

A cityscape with modern skyscrapers and a curved highway.

West Loop

Consider a visit to The Old Post Office and take some time to enjoy the abundant dining options during your time in West Loop. If you want to see more of the city, jump on the metro at Racine Station or Ogilvie Transportation Center.

Our pick of the best Downtown Chicago Hotel Deals

River Hotel

75 East Wacker Drive Chicago IL

Fully refundableReserve now, pay when you stay

NZ$364

20 Sept - 21 Sept

includes taxes & fees

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

NZ$370

13 Oct - 14 Oct

includes taxes & fees

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

NZ$355

27 Sept - 28 Sept

includes taxes & fees

8/10 Very good! (10,264 reviews)

"Clean room, funky smell tho. Super nice staff. Very helpful"

Reviewed on 17 Sept 2026

See all 1,602 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 holiday package cost?

Go from looking to booking with our Downtown Chicago holiday packages, which start from just NZ$1,333. 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 holiday 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 holiday you've always dreamed of in Downtown Chicago is much closer than you thought!

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

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 holiday package?

Yes — that's the beauty of an Expedia holiday 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 holiday 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 holiday 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)

One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.

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A large metallic sphere sculpture in a public square surrounded by tall buildings.

Millennium Park

9.4/10 (30,446 reviews)

See mind-bending sculptures, a musically-inspired lawn and giant water fountains that double-up as video screens.

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A cityscape at night with illuminated buildings, a river, and a bridge.

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 city street at night with illuminated buildings, a prominent tower, and decorated trees.

Michigan Avenue

9.4/10 (15,813 reviews)

You can find the perfect gifts to bring home 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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