Miles Vacations from $368

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The Latest Miles vacation packages

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $609, price is now $368 per person
$368
per person
Mar 4 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
The only downfall here was the valet parking. They give you a ticket to call ahead but then you get to the front and THEN they have someone go get a car 15+ minutes away. Some days only one kid is working and has multiple cars to get and bring back. Obviously not his fault! But the process needs tweaking and is frustrating. Also, wouldn’t necessarily recommend for a family with small kids. But it did what it needed to for our stay.

Reviewed on Dec 30, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $830, price is now $476 per person
$476
per person
Mar 4 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Good for a girls night out where we had access to bars and dining. Pricey for what you get, room was small, beds were comfy. Good for a night out downtown

Reviewed on Dec 29, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $752, price is now $441 per person
$441
per person
Mar 4 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Staff was friendly did amazing job with checking us in

Reviewed on Dec 25, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $657, price is now $386 per person
$386
per person
Mar 4 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Jasmine was courteous and friendly, made our check in process smooth. Clean rooms and the breakfast was amazing. I definitely recommend staying here.

Reviewed on Dec 31, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $775, price is now $460 per person
$460
per person
Mar 4 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Everything was great!

Reviewed on Dec 29, 2025

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Miles Hotel Deals

Stoney Creek Inn Galena

Stoney Creek Inn Galena

2 out of 5
940 Galena Square Dr Galena IL
Fully refundable
$88 nightly
The price is $98 total per night from Jan 5 to Jan 6
$98 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
9.2/10 Wonderful! (1,296 reviews)
Cozy and have a charater

Reviewed on Dec 28, 2025

Stoney Creek Inn Galena
Chestnut Mountain Resort

Chestnut Mountain Resort

3 out of 5
8700 W Chestnut Mountain Rd Galena IL
$102 nightly
The price is $114 total per night from Jan 4 to Jan 5
$114 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.4/10 Very Good! (1,000 reviews)
Very happy top to bottom!

Reviewed on Dec 24, 2025

Chestnut Mountain Resort
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
$95 nightly
The price is $105 total per night from Jan 14 to Jan 15
$105 total
Jan 14 - Jan 15, 2026
Total with taxes and fees
9.2/10 Wonderful! (1,001 reviews)
The room was clean, staff was real

Reviewed on Dec 25, 2025

Country Inn & Suites by Radisson, Galena, IL
See all 720 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 $368 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.