Downtown Chicago Vacation Packages 2026 from NT$43,751

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The Latest Downtown Chicago Vacation Packages

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

The Emily Hotel

Downtown Chicago

NT$43,751

per person

Jan 23 - Jan 26

found 2 hours ago

Roundtrip non-stop flight included

Taipei (TPE) to Chicago (ORD)

9.2/10 Wonderful! (1,358 reviews)

Hotel Riu Plaza Chicago

Downtown Chicago

NT$46,738

per person

Jan 23 - Jan 26

found 2 hours ago

Roundtrip non-stop flight included

Taipei (TPE) to Chicago (ORD)

9.4/10 Exceptional! (5,555 reviews)

Great location, nice rooms, nice rooftop bar and large breakfast buffet included.

Reviewed on 2026/10/28

Trump International Hotel & Tower Chicago

Downtown Chicago

NT$53,150

per person

Jan 23 - Jan 26

found 2 hours ago

Roundtrip non-stop flight included

Taipei (TPE) to Chicago (ORD)

9.6/10 Exceptional! (2,057 reviews)

Level Chicago - River North

Downtown Chicago

NT$48,342

per person

Jan 23 - Jan 26

found 2 hours ago

Roundtrip non-stop flight included

Taipei (TPE) to Chicago (ORD)

9.2/10 Wonderful! (1,149 reviews)

What a fun and unique stay… a condo where non-sold units are rented. Spotlessly clean, think never lived in (but had been occupied), digital security to maximize safety at all times, located in a hip and vibrant River North neighborhood - lovely restaurants/bars, spas, shopping, etc. On-site parking, staff most helpful (love Joy - the evening auditor). The amenities including gym, rooftop gathering and more….slept like a rock with the bedroom windows open to the balcony….little noise. A perfect stay at a fantastic rate. With Expedia gold membership saved 83%. Check out the space and the Expedia app for bookings!

Reviewed on 2026/10/28

The Talbott, Autograph Collection

Downtown Chicago

NT$45,036

per person

Jan 23 - Jan 26

found 2 hours ago

Roundtrip non-stop flight included

Taipei (TPE) to Chicago (ORD)

9.4/10 Exceptional! (185 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 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.

Downtown Chicago Hotel Deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

NT$3,764

NT$4,475 total

Nov 11 - Nov 12

includes taxes & fees

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

NT$4,343

NT$5,164 total

Nov 9 - Nov 10

includes taxes & fees

River Hotel

75 East Wacker Drive Chicago IL

Fully refundableReserve now, pay when you stay

NT$3,761

NT$4,471 total

Nov 23 - Nov 24

includes taxes & fees

8.8/10 Excellent! (5,570 reviews)

"The rooms need a deep clean, they were clean but stained on the ceiling and carpets. Bed was very worn. Staff were all very nice, from check in to seeing staff in the elevator!"

Reviewed on 2026/10/29

See all 1,608 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$43,751. 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.