Miles Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Richard Remington
    deals illustration

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    stays illustration

    Find the right fit

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

    Rest easy

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

Top Miles Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 4 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
I loved the location of the property, and the overall concept of something fun and funky, but I had a "higher end" room, and it was right near the elevator, so I got a lot of noise on that side, plus the El from the other side. The rug wasn't super clean (although the bedding and the rest of the room were a delight). The most annoying thing was the TV. Anything I turned it to, 10 minutes later to the minute, it went back to the Virgin channel #1, here are all our hotels in the world. I really hated having to stay on top of a show, when usually I want the tv on as background while I'm getting ready, etc. Also, this hotel's amenities were oversold, i.e., good luck getting on the rooftop, especially if you just wanted a quiet sip of a drink. I loved the cafe and the staff, though, everyone was very pleasant.

Reviewed on Jul. 15, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 4 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Amazing customer service

Reviewed on Jul. 13, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Superb customer service, clean hotel!

Reviewed on Jun. 13, 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 4 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (639 reviews)
Amazing amenities. friendly staff and clean rooms. Views from the balcony were so nice!

Reviewed on Jul. 12, 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
Save 100% on your flight
per person
Sep 4 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,053 reviews)
Wonderful views from navy pier.

Reviewed on Jul. 14, 2025

Ready to book your vacation to Miles?

 

Choose your dates

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
The price is CA $134 per night from Jul 16 to Jul 17
CA $134
CA $149 total
Jul 16 - Jul 17
includes taxes & fees
9.2/10 Wonderful! (1,197 reviews)
"This is an outstanding motel. A custom feel throughout with theme lamps and other touches that show refined taste. A gem. Highly recommended."

Reviewed on Jul. 11, 2025

Stoney Creek Inn Galena
Irish Cottage Inn & Suites

Irish Cottage Inn & Suites

3.5 out of 5
9853 US-20, Galena, IL
The price is CA $135 per night from Jul 21 to Jul 22
CA $135
CA $188 total
Jul 21 - Jul 22
includes taxes & fees
9.4/10 Exceptional! (1,142 reviews)
"Staff was friendly. Great location. Restaurant attached was fantastic."

Reviewed on Jul. 11, 2025

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
The price is CA $136 per night from Jul 28 to Jul 29
CA $136
CA $151 total
Jul 28 - Jul 29
includes taxes & fees
9.2/10 Wonderful! (1,018 reviews)
"Great for kids, has an arcade, nice swim area for kids, 2 pools"

Reviewed on Jul. 13, 2025

Country Inn & Suites by Radisson, Galena, IL
See all 694 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Miles vacation package cost?
You can pick up a vacation package to this top destination from CA $1,026 on Expedia. However, how much your vacation to Miles costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Miles?
If you're looking to snag a cheap Miles vacation package, consider travelling in January, February and April. You'll generally find better rates on flights and accommodations during these quieter months --- ideal for a budget-friendly getaway.
How many days is enough for Miles?
With a well-organized itinerary, you can easily hit the top Miles attractions in a few days. But if you want to venture off the beaten track or take day trips, consider booking your Miles vacation for longer.
How to find the best Miles package deals?
Begin your search for a Miles package deal by entering your destination and travel dates under our "Packages" tab. Then apply some filters, like "Property type" and "Popular locations," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal Miles package deal right away, simply tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Miles escape off to a flying start.
Is it cheaper to book a Miles vacation as a package?
You can enjoy significant savings on your next Miles escape by booking a customized vacation package. Click on the "Package" heading, then enter your destination and travel dates to browse some great airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Miles?
If you have your Miles vacation dates finalized, book as early as you can to grab some terrific deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for quick escapes.
How to plan a trip to Miles?

  1. Choose when to go: Check your calendar and get your bags packed. Your favourite season and the available activities will also help you decide when to escape to Miles.
  2. Set your budget: Consider costs such as flights, food and transportation when working out how much to save for your trip to Miles. Then, pick a property that works with your budget, whether that's a low-cost option or a swankier getaway.
  3. Decide your trip length: Consider how much time you want to spend discovering Miles. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a comfortable pace.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to choose 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.