Miles Vacations from $352

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The Latest Miles vacation packages

Price found within the past 48 hours. Click for updated prices.
Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Downtown Chicago
Price was $506, price is now $352 per person
$352
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
I really loved this hotel. The rooms were clean and spacious. The staff was nice and helpful James was especially great. The restaurant staff was very helpful. When I visit again I'll stay here. And it was close to everything.

Reviewed on Nov 3, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $1,182, price is now $718 per person
$718
per person
Jan 23 - Jan 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,358 reviews)

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

3.5 out of 5
Price was $1,148, price is now $725 per person
$725
per person
Dec 16 - Dec 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.6/10 Excellent! (1,005 reviews)

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 $1,604, price is now $1,044 per person
$1,044
per person
Jan 23 - Jan 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,739 reviews)

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was $947, price is now $622 per person
$622
per person
Jan 23 - Jan 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (591 reviews)

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Miles Roadside Park

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Miles Hotel Deals

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
$98 nightly
The price is $109 total per night from Dec 13 to Dec 14
$109 total
Dec 13 - Dec 14
Total with taxes and fees
9.4/10 Exceptional! (1,531 reviews)
"Loved the theme and the entire property. Dinner at Frank O'Dowd's was also amazing."

Reviewed on Nov 11, 2026

Irish Cottage Inn & Suites
Country Inn & Suites by Radisson, Galena, IL

Country Inn & Suites by Radisson, Galena, IL

2.5 out of 5
11334 Oldenburg Ln Galena IL
Fully refundable
$81 nightly
The price is $90 total per night from Dec 10 to Dec 11
$90 total
Dec 10 - Dec 11
Total with taxes and fees
Country Inn & Suites by Radisson, Galena, IL
Stoney Creek Inn Galena

Stoney Creek Inn Galena

2 out of 5
940 Galena Square Dr Galena IL
Fully refundable
$96 nightly
The price is $107 total per night from Dec 1 to Dec 2
$107 total
Dec 1 - Dec 2
Total with taxes and fees
Stoney Creek Inn Galena
See all 833 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.

Find the Best Miles Vacation Packages

Miles Essential Information

Language
English
Currency
U.S dollars

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Frequently asked questions

How much does a Miles vacation package cost?
You can snap up a vacation package to this popular destination from $352 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?
If you're looking to snag a cheap Miles vacation package, consider traveling in November, December and January. You'll typically find better rates on flights and accommodations during these quieter months — ideal for budget-conscious travelers.
How many days is enough for Miles?
Generally, a handful of days is enough to go to the major sights during your Miles vacation. But if you prefer to have more time to chill out or go on day trips, think about extending your trip.
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.
Does Expedia offer Book Now, Pay Later Miles vacation packages?
If you're like us, you love going away but don't love the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Miles trip across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.