Downtown Chicago Vacation Packages 2026 from NT$21,422

The Latest Downtown Chicago Vacation Packages

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

Hotel Felix River North/Magnificent Mile

Downtown Chicago

Save 100% on your flight

NT$21,422

per person

Jul 23 - Jul 26

found 3 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

8.2/10 Very Good! (2,779 reviews)

the only issue i had it was that they didn’t do room service in the room, no new towels , no toilet paper and stuff like that

Reviewed on 2026/6/12

Pendry Chicago

Downtown Chicago

Save 100% on your flight

NT$34,672

per person

Jul 23 - Jul 26

found 3 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,119 reviews)

Great staff and property!

Reviewed on 2026/6/10

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

NT$37,677

per person

Jul 23 - Jul 26

found 3 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.6/10 Exceptional! (1,893 reviews)

The fitness center & spa was top notch. The on site restaurant had amazing food and service.

Reviewed on 2026/6/12

Eurostars Magnificent Mile

Downtown Chicago

Save 100% on your flight

NT$23,517

per person

Jul 23 - Jul 26

found 3 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (3,634 reviews)

It is well placed. Good breakfasts

Reviewed on 2026/6/13

Omni Chicago Hotel

Downtown Chicago

Save 100% on your flight

NT$27,292

per person

Jul 23 - Jul 26

found 3 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,791 reviews)

Pro: Good gym, good room size, 676 restaurant. Con: room 1610 by the elevator is extremely noisy. Plus slow elevators. Late checkout charge, even though I'm a member. Shower pressure was like a fire hose, water everywhere.

Reviewed on 2026/6/12

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

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.

Downtown Chicago Hotel Deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

NT$4,301

NT$5,113 total

Jun 29 - Jun 30

includes taxes & fees

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

"Great stay!"

Reviewed on 2026/6/14

The Chicago Hotel Collection - Magnificent Mile

166 E Superior Street Chicago IL

Fully refundable

NT$4,566

NT$5,429 total

Jun 30 - Jul 1

includes taxes & fees

7.8/10 Good! (1,578 reviews)

"Had a great time over two days in Chicago. The only downside was that my room was not cleaned when I returned."

Reviewed on 2026/6/14

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

NT$4,944

NT$5,878 total

Jun 29 - Jun 30

includes taxes & fees

8.2/10 Very Good! (1,602 reviews)

"This review reflects both the hotel and Expedia’s handling of the booking. The good: The location is excellent and very accessible. The common areas, including the lobby and bar, are pleasant and well maintained. The bad: The hotel is showing its age. The AC struggled to keep the room comfortable ..."

Reviewed on 2026/6/13

See all 1,622 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 NT$21,422. 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.