Miles Vacations from $420

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The Latest Miles vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $676, price is now $420 per person
$420
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Rooms and public areas newly remodeled; Rooftop bar and restaurant were unexpectedly good.

Reviewed on Sep 20, 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $962, price is now $573 per person
$573
per person
Nov 21 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,014 reviews)
Convenient location for what we were doing. Highly suggested if you are going to a show at the Chicago Theater.

Reviewed on Sep 17, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,248, price is now $772 per person
$772
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
This property is fabulous in every aspect. Huge rooms, modern and fresh. The spa and workout facilities are amazing. I loved everything about this hotel. Location is perfect to explore the river walk, shopping and best dining options. Only small critique is only one person at the front and if they are busy with a guest, can be a long wait to check in or out.

Reviewed on Sep 21, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,045, price is now $647 per person
$647
per person
Nov 21 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
The hotel is beautiful! Great staff and perfect location

Reviewed on Sep 20, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,073, price is now $686 per person
$686
per person
Nov 21 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
This is an exceptional hotel. The rooms are clean. The service is impeccable, and the products!! The signature scent is to die for. It is now a part of my life. I had to buy a candle on the way out and have already visited the online store for body wash and lotion. Well done. There are a lot of choices in Chicago, but this is now my go to. Will definitely be back!

Reviewed on Sep 12, 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 Sep 29 to Sep 30
$98 total
Sep 29 - Sep 30
Total with taxes and fees
9.2/10 Wonderful! (1,222 reviews)
"Everything was great"

Reviewed on Sep 19, 2025

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
$143 nightly
The price is $159 total per night from Sep 22 to Sep 23
$159 total
Sep 22 - Sep 23
Total with taxes and fees
9.4/10 Exceptional! (1,199 reviews)
"Spacious rooms. Felt like an Irish cottage"

Reviewed on Sep 17, 2025

Irish Cottage Inn & Suites
Chestnut Mountain Resort

Chestnut Mountain Resort

3 out of 5
8700 W Chestnut Mountain Rd, Galena, IL
$98 nightly
The price is $109 total per night from Oct 21 to Oct 22
$109 total
Oct 21 - Oct 22
Total with taxes and fees
8.4/10 Very Good! (1,006 reviews)
"We had a very nice time we love it there will definitely come back just nice walking around and seeing the scenery"

Reviewed on Sep 18, 2025

Chestnut Mountain Resort
See all 708 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.

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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 $420 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.