Miles Vacation Packages

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Miles Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
Oct 23 - Oct 26
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,149 reviews)
Moments after arriving the hotel room, I took a shower and when I got out, there was a cockroach on my floor near the bed.

Reviewed on Aug. 7, 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
per person
Oct 17 - Oct 22
just found
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (652 reviews)
Quick and easy check in. Parking in their private garage was breeze. Plenty of space, mostly empty, and our vehicle could stay in the garage until 2:00 PM the next day. Beautiful 1 BR condo. Full kitchen, beautiful views of the city on the balcony and from the living room, and very clean space overall. Need your key card for just about everything (pool, lounge, some of the outdoor bathrooms, elevators, etc.).

Reviewed on Jul. 27, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Loved the attention to details that made the experience exceptional.

Reviewed on Aug. 6, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,270 reviews)
The Breakfast Buffet ( included with your stay ) was a real surprise. Reminded us of the ones when we stay at all inclusive resorts when it comes to breafast options. The food was fantastic and the staff was very attentive cleaning and seating everyone quickly. Rooms were really nice, comfortable bed, bathroom was laid out really well. Super clean hotel that we would definitely recommend & stay at again when returning to Chicago

Reviewed on Aug. 7, 2025

Art Villa

Art Villa

5 out of 5
West Town
per person
Oct 17 - Oct 22
just found
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
10/10 Exceptional! (1 review)

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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 refundableReserve now, pay when you stay
The price is CA $135 per night from Aug 24 to Aug 25
CA $135
CA $150 total
Aug 24 - Aug 25
includes taxes & fees
9.2/10 Wonderful! (1,206 reviews)
"Clean, friendly staff."

Reviewed on Aug. 5, 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
The price is CA $117 per night from Aug 11 to Aug 12
CA $117
CA $169 total
Aug 11 - Aug 12
includes taxes & fees
9.4/10 Exceptional! (1,157 reviews)
"Live music and atmosphere of pub and character of building"

Reviewed on Aug. 5, 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 $138 per night from Aug 25 to Aug 26
CA $138
CA $154 total
Aug 25 - Aug 26
includes taxes & fees
9.2/10 Wonderful! (1,006 reviews)
"The kids really enjoyed the pool area."

Reviewed on Aug. 4, 2025

Country Inn & Suites by Radisson, Galena, IL
See all 696 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 pick up a vacation package to this top destination from CA $922 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.