Downtown Chicago Vacations from ￥152,165

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The Latest Downtown Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Eaglewood Resort and Spa

Eaglewood Resort and Spa

4 out of 5
Price was ￥170,800, price is now ￥152,165 per person
￥152,165
per person
Feb 12 - Feb 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,004 reviews)
I was so disappointed and disgusted with the stains all over the chair in the room. When I reported it all I got was I won’t be charged for damages. I really liked the stay overall I was just very disappointed with this situation

Reviewed on Jan 1, 2026

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was ￥241,345, price is now ￥196,404 per person
￥196,404
per person
Feb 12 - Feb 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
Great stay fir early flights

Reviewed on Jan 8, 2026

Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Downtown Chicago
Price was ￥294,574, price is now ￥252,916 per person
￥252,916
per person
Mar 29 - Apr 4
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,159 reviews)
Great location. Good size room. Restaurant was awesome.

Reviewed on Jan 9, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was ￥319,399, price is now ￥278,176 per person
￥278,176
per person
Mar 29 - Apr 4
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
The room was spacious and the amenities great. Food was good both at the cafe and in the restaurant. Good location

Reviewed on Jan 9, 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was ￥505,006, price is now ￥445,327 per person
￥445,327
per person
Mar 29 - Apr 4
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Upon check-in, it was magical! The doormen were amazing, the 'go as often as you'd like' Santa's candy shop, overall hotel decorations and the professionalism of the staff will blow you away!!! This hotel is next level up and puts the Ritz Carlton down a notch, for sure. Our room was truly magnificent and I wish we could have stayed longer!

Reviewed on Jan 6, 2026

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 - River North

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.

Find hotels in Magnificent Mile

Downtown Chicago Hotel Deals

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥22,386 per night from Jan 17 to Jan 18
￥22,386
￥30,201 total
Jan 17 - Jan 18
includes taxes & fees
8.4/10 Very Good! (2,223 reviews)
Room was very clean and staff was great

Reviewed on Jan 6, 2026

Palmer House a Hilton Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥21,743 per night from Jan 17 to Jan 18
￥21,743
￥30,129 total
Jan 17 - Jan 18
includes taxes & fees
8.4/10 Very Good! (2,507 reviews)
Clean, good breakfast, quiet. Easy acces

Reviewed on Jan 9, 2026

Hilton Chicago
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥14,024 per night from Jan 18 to Jan 19
￥14,024
￥16,463 total
Jan 18 - Jan 19
includes taxes & fees
8.8/10 Excellent! (3,677 reviews)
Room and hotel overall very clean. Noted some things that could be updated in bathroom(stopper in sink didnt go all the way down, peeling caulk and some missing grout). Minor updates. Our sink was clogged when we checked in and I called the front desk, housekeeping and the hotel hotline 4 different ...

Reviewed on Jan 7, 2026

Hilton Chicago/Magnificent Mile Suites
See all 1,720 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 ￥152,165. 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.

Discover the most popular places to visit in Downtown Chicago

Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier featuring a sunset and rides

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Millennium Park featuring a city, modern architecture and fall colors

Millennium Park

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park

Things to do

Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

￥6,889
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,845
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

￥6,263
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.