Downtown Chicago Holidays & Package Deals

Your Downtown Chicago Holiday

Reserving a Downtown Chicago holiday package is a great way to get to know this unique neighbourhood. From its must-visit places to its lesser-known delights, you'll be sure to uncover something new. Some leading nearby attractions to see during your trip to Downtown Chicago include Millennium Park, Willis Tower and Art Institute of Chicago. Whatever your travel plans or the size of your budget, booking your dream Downtown Chicago holiday is a cinch with Expedia.

Top Holiday Package Deals in Downtown Chicago

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

Embassy Suites by Hilton Chicago O'Hare Rosemont

AU$2,350

per person

2 Sept - 9 Sept

found 1 day ago

Return flight included

Sydney (SYD) to Chicago (ORD)

8.8/10 Excellent! (1,453 reviews)

Room was clean. Breakfast was great. Site was close to entertaining area with many restaurants, movies.

Reviewed on 25 June 2026

Level Chicago Fulton Market

Downtown Chicago

AU$3,029

per person

2 Sept - 9 Sept

found 1 day ago

Return flight included

Sydney (SYD) to Chicago (ORD)

9.2/10 Wonderful! (504 reviews)

Upscale amazing stay in trendy neighborhood in Chcago. Walking distance to coffee shops, great restaurants. The amenities were beyond what I expected/ great lap pool, hot tubs, sauna steam room and amazing gym with enough equipment to do a full strength training workout. We will stay here again!

Reviewed on 25 June 2026

Hilton Chicago O'Hare Airport

O'Hare

AU$2,856

per person

2 Sept - 9 Sept

found 1 day ago

Return flight included

Sydney (SYD) to Chicago (ORD)

8.4/10 Very good! (2,349 reviews)

Clean room, staff were very helpful and very friendly. Restaurants and bar were on point. Great experience! Thanks Hilton Chicago O’Hare Airport!

Reviewed on 25 June 2026

Hilton Rosemont Chicago O'Hare

AU$2,689

per person

2 Sept - 9 Sept

found 1 day ago

Return flight included

Sydney (SYD) to Chicago (ORD)

8.4/10 Very good! (1,005 reviews)

The stay was good, the service at the restaurant was excellent.

Reviewed on 23 June 2026

Courtyard by Marriott Chicago O'Hare

AU$2,470

per person

2 Sept - 9 Sept

found 1 day ago

Return flight included

Sydney (SYD) to Chicago (ORD)

8.4/10 Very good! (1,015 reviews)

Todo bien solo la piscina estuvo cerrada el fin de semana

Reviewed on 22 June 2026

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

A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.

Our pick of the best Downtown Chicago Hotel Deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

AU$235

29 June - 30 June

includes taxes & fees

8/10 Very good! (10,132 reviews)

"The hotel is a bit run down, but my room was very clean. The breakfast was good, although it is not included, and for some reason I thought it was. The receptionist was amazing. She was very kind and allowed me to check in early, which I really appreciated. The location is also excellent. I’m giving ..."

Reviewed on 26 June 2026

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl Chicago IL

Fully refundableReserve now, pay when you stay

AU$275

6 July - 7 July

includes taxes & fees

9/10 Wonderful! (4,461 reviews)

"Great stay. Convenient to where we wanted to go and easy access to the bus"

Reviewed on 26 June 2026

Hotel Riu Plaza Chicago

150 East Ontario Street Chicago IL

Fully refundableReserve now, pay when you stay

AU$349

5 July - 6 July

includes taxes & fees

9.4/10 Exceptional! (4,542 reviews)

"There isnt a vending machine with drinks or snacks. I had to walk a block to 7-11 at night. That was my only complaint. Other than that my say was awesome."

Reviewed on 26 June 2026

See all 1,682 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 AU$2,350. 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.