Miles Vacations from ￥316,532

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    Save up to ￥45,448 when you book a flight and hotel together*
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The Latest Miles Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥435,978, price is now ￥316,532 per person
￥316,532
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,061 reviews)
Understaffed but staff was nice. Tiny rooms.

Reviewed on Aug 23, 2025

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
Price was ￥485,550, price is now ￥331,810 per person
￥331,810
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,014 reviews)
Loved the hotel. Very clean and comfortable. The gentleman who checked us out was not the most friendly, but everyone else was super helpful!

Reviewed on Aug 18, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was ￥616,874, price is now ￥443,960 per person
￥443,960
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.

Reviewed on Aug 19, 2025

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥445,492, price is now ￥323,058 per person
￥323,058
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (3,059 reviews)
Loved the property, big size room and very cool decoration! Great location

Reviewed on Aug 22, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was ￥456,478, price is now ￥332,201 per person
￥332,201
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,087 reviews)
Staff was amazing!! Everything was so easy checking in and checking out. The stay was great! It was so nice having the pier to ourselves after hours.

Reviewed on Aug 20, 2025

Find the Best Miles Vacation Packages

Miles Hotel Deals

Stoney Creek Inn Galena

Stoney Creek Inn Galena

2 out of 5
940 Galena Square Dr, Galena, IL
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (1,210 reviews)
"Loved this Inn! Super rustic feel and clean!"

Reviewed on Aug 18, 2025

Get rates
Stoney Creek Inn Galena
Irish Cottage Inn & Suites

Irish Cottage Inn & Suites

3.5 out of 5
9853 US-20, Galena, IL
Fully refundableReserve now, pay when you stay
The price is ￥13,549 per night from Aug 25 to Aug 26
￥13,549
￥19,115 total
Aug 25 - Aug 26
includes taxes & fees
9.4/10 Exceptional! (1,174 reviews)
"We really enjoyed the whole vibe. The bar was a bit pricey, but has an amazing feel. It served us very well as a home base in our stay in Galena, and had us within short drives to all the places we wanted to visit. Potosi, Dubuque, Effegy Mounds and of course downtown Galena."

Reviewed on Aug 21, 2025

Irish Cottage Inn & Suites
Chestnut Mountain Resort

Chestnut Mountain Resort

3 out of 5
8700 W Chestnut Mountain Rd, Galena, IL
8.4/10 Very Good! (1,002 reviews)
"Beautiful resort, helped me with last minute booking and everything went smoothly"

Reviewed on Aug 11, 2025

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Chestnut Mountain Resort
See all 697 properties in Miles
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 Miles vacation package cost?
You can snap up a vacation package to this popular destination from ￥316,532 on Expedia. But how much your vacation to Miles costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Miles?
You can generally find lower prices and better availability in January, February and April. Explore our cheap Miles vacation packages and you could get some great off-season discounts.
How many days is enough for Miles?
With a well-planned itinerary, you can easily visit the main Miles attractions in a few days. But if you'd like to venture off the beaten track or go on day trips, think about booking your Miles vacation for longer.
How to find the best Miles package deals?
Use Expedia's filters to find some terrific Miles package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Miles package deals in the off-season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Miles vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging flights and hotels individually. Better still, you can customize your Miles trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Miles?
If you're planning a spontaneous Miles trip, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land incredible deals on your hotels and flights by booking well in advance.
How to plan a trip to Miles?

  1. Choose when to travel: Check your calendar and get packing. Your preferred time of year and the activities available will also help you decide when to vacation in Miles.
  2. Figure out your budget: Make sure you have enough money to cover everything from dining out and transportation to airfares and activities. Your hotel will likely be the largest expense during your trip to Miles.
  3. Work out your trip length: Consider how much time you want to spend exploring Miles. Plan your days so you can get to all the attractions and activities you're interested in without rushing.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to find a Miles vacation package that brings all your bookings together.

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