Magnificent Mile Vacations from ￥299,263

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  • Plan, book, travel with confidence

  • Better together

    Save up to ￥45,448 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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    Plan, book, and manage your trip all in one place

The Latest Magnificent Mile Vacation Packages

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

The Wade

4.5 out of 5
Downtown Chicago
Price was ￥413,928, price is now ￥299,263 per person
￥299,263
per person
May 14 - May 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (1,700 reviews)
Room was very clean would return again

Reviewed on Feb 23, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was ￥511,987, price is now ￥326,534 per person
￥326,534
per person
May 14 - May 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
This Hotel is the re-l deal! Right by Michigan avenue within close distance to magnificent mile and multiple attractions. Breakfast was great and accomodations were great. Highly recommend!

Reviewed on Mar 2, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was ￥464,738, price is now ￥323,424 per person
￥323,424
per person
May 14 - May 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Room smelled like food but overall very clean, very great service and staff both night and morning shift.

Reviewed on Feb 16, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was ￥618,362, price is now ￥443,394 per person
￥443,394
per person
May 14 - May 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room was ready at 9am, the room and view was amazing. Housekeeping and turn down service was also great. Customer service was fantastic and so is the location of the hotel.

Reviewed on Feb 28, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was ￥454,048, price is now ￥327,960 per person
￥327,960
per person
May 14 - May 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Had a great stay!! Kelly at the front desk was so sweet

Reviewed on Feb 22, 2026

Where to stay in Magnificent Mile

Find the best Magnificent Mile areas and neighborhoods for the activities you enjoy most. Learn more about Magnificent Mile
Downtown Chicago showing a city

Downtown Chicago

4 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Magnificent Mile Hotel Deals

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave Chicago IL
The price is ￥27,777 per night from Mar 15 to Mar 16
￥27,777
￥37,601 total
Mar 15 - Mar 16
includes taxes & fees
9.2/10 Wonderful! (2,842 reviews)
Me and my Bestfriend had a great time! Hotel was superr convenient. In and out was a fast and easy process. I’d love to stay again while visiting Chicago.

Reviewed on Mar 2, 2026

InterContinental Chicago Magnificent Mile by IHG
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
909 North Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥21,067 per night from Mar 15 to Mar 16
￥21,067
￥29,413 total
Mar 15 - Mar 16
includes taxes & fees
8.8/10 Excellent! (1,113 reviews)
Spotless room, helpful staff, excellent location

Reviewed on Feb 20, 2026

The Westin Michigan Avenue Chicago
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 ￥26,965 per night from Mar 27 to Mar 28
￥26,965
￥31,656 total
Mar 27 - Mar 28
includes taxes & fees
8/10 Very Good! (9,903 reviews)
The room was cold, temperature in room was about 63 degrees, front desk sent up maintenance engineer, temperature never got any warmer, had to sleep in our clothes with coats.

Reviewed on Mar 2, 2026

Congress Plaza Hotel
See all 1,122 properties in Magnificent Mile
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 Magnificent Mile vacation package cost?
Create unforgettable memories with our Magnificent Mile vacation packages, which start from only ￥299,263. Choose the hotels and flights that match your travel plans. Then, add on one or two tours or experiences for an incredible getaway.
How do I get a cheap travel package to Magnificent Mile?
Browse and book everything in one place with our Magnificent Mile vacation packages. We have deals on flights, hotels and more that'll keep your hip pocket happy and your adventurous spirit alive. And, with more than 550 partner airlines and 1,000,000 hotel options around the world to pick from, there are endless opportunities to mix and match all you want.
Where should I stay in Magnificent Mile?
Take the leg work out of sightseeing by staying in a hotel just around the corner from Magnificent Mile's biggest attractions. McCormick Place and Millennium Park are two of the most popular.
What are the top hotels in Magnificent Mile?
If it's your first time in Magnificent Mile, make a reservation at InterContinental Chicago Magnificent Mile, an IHG Hotel or The Westin Michigan Avenue Chicago. Both hotels offer friendly service and are favorites with many travelers.
How far in advance should I book my Magnificent Mile vacation?
Reserving your flights early with Expedia means one less thing to worry about. A number of air carriers advertise tickets up to 12 months prior to take off. Typically, this is the cheapest time to book. If circumstances have left you booking late, low prices to Magnificent Mile sometimes become available in the weeks leading up to departure.
What does an Expedia Magnificent Mile travel package include?
Expedia has all you need to book your Magnificent Mile escape, but what your package looks like depends on you. Pick from any combination of rental cars, flights and hotels. Looking for some tours or activities to fill in your time? Once you've made your booking, you can add them on too. No matter your budget or style, there's a package to meet your needs.
What should I know before booking a Magnificent Mile travel package?
Booking all the parts of your trip together is one of the best ways to save. Bundle your flights, car rentals and hotels into one little package. But it's not just hotels. Expedia features all types of properties, including vacation rentals such as beachfront villas and city residences. You've got loads of choices!
Can I choose my airline with a Magnificent Mile Expedia vacation package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines worldwide. Our packages give you the flexibility to pick from available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Magnificent Mile vacation package?
Because we know life can throw you a few curveballs, the answer is yes. For more information, check out our Customer Service Portal. But generally speaking, if you've booked your Magnificent Mile vacation package in the last 24 hours, you may be able to cancel or change it without penalty. Your hotel, airline or car rental company may charge a fee if your booking is older than that.

Things to do

Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

￥6,810
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

￥6,191
per adult
92% of travellers recommend
Art Institute of Chicago
Flyover in Chicago

Flyover in Chicago

￥5,885
per adult
98% of travellers recommend
Flyover in 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.