Downtown Chicago Vacations from NT$21,422

Book a Hotel + Flight or Car together to unlock savings

The Latest Downtown Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Pendry Chicago
Trump International Hotel & Tower Chicago
Eurostars Magnificent Mile
Omni Chicago Hotel

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

Downtown Chicago Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is NT$4,301 per night from Jun 29 to Jun 30
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

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is NT$4,566 per night from Jun 30 to Jul 1
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 - Magnificent Mile
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is NT$4,944 per night from Jun 29 to Jun 30
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

The Chicago Hotel Collection Ambassador Gold Coast
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.

Stay near popular Downtown Chicago attractions

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.