Eagle Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together
    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Your Eagle Vacation

When a city escape is calling, answer it with a vacation package to Eagle. With all your travel arrangements taken care of before you leave, all you have to do here is concentrate on enjoying yourself. Make sure to spend time sightseeing during your trip to Eagle. Kettle Moraine Ranch and Old World Wisconsin are some top attractions to visit. No matter your travel plans or the size of your budget, putting together a tailored Eagle vacation is simple with Expedia.

Top Eagle Vacation Deals

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

Hilton Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (1,950 reviews)
The property was very nice until we got to the room. The room seemed more dark and dingy. Very expensive for the quality of the room. Staff were extremely nice and the hotel was more central to different parks and modes of transportation.

Reviewed on Jul. 2, 2025

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 8 - Aug 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,274 reviews)
The staff was very nice. Everything went well my view of Navy Pier and the lake was beautiful. Only problem was The Palm. The food was excellent, but staff was quite biased.

Reviewed on Jul. 6, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
Superb customer service, clean hotel!

Reviewed on Jun. 13, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Great place! Will be back!

Reviewed on Jul. 6, 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 25 - Sep 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,623 reviews)
This was our second stay here. We were particularly impressed by the staff and customer service. It’s the kind we get in 5stars hotels overseas in the Middle East or SouthEast Asia. Impeccable. A special shout out to Pablo Criado for his warm and enthusiastic welcome and making sure that we had a great stay! I am now a fan and will only stay at Trump Chicago when in Chicago downtown.

Reviewed on Jul. 5, 2025

Ready to book your vacation to Eagle?

 

Choose your dates

Eagle Hotel Deals

Sonesta Select Milwaukee Brookfield
Sonesta Select Milwaukee Brookfield
3 out of 5
16865 W Bluemound Rd, Brookfield, WI
Fully refundableReserve now, pay when you stay
The price is CA $112 per night from Jul 28 to Jul 29
CA $112
CA $129 total
Jul 28 - Jul 29
includes taxes & fees
8/10 Very Good! (1,123 reviews)
Nice hotel, reasonable price
"Everything was good. My only complaint was that there was a large sticky spot on the carpet."

Reviewed on Jul. 1, 2025

Sonesta Select Milwaukee Brookfield
Harbor Shores on Lake Geneva
Harbor Shores on Lake Geneva
3.5 out of 5
300 Wrigley Dr, Lake Geneva, WI
Fully refundableReserve now, pay when you stay
The price is CA $202 per night from Aug 5 to Aug 6
CA $202
CA $258 total
Aug 5 - Aug 6
includes taxes & fees
9/10 Wonderful! (1,184 reviews)
"Clean great staff"

Reviewed on Jul. 3, 2025

Harbor Shores on Lake Geneva
Sheraton Milwaukee Brookfield Hotel
Sheraton Milwaukee Brookfield Hotel
3.5 out of 5
375 S Moorland Rd, Brookfield, WI
Fully refundableReserve now, pay when you stay
The price is CA $118 per night from Jul 20 to Jul 21
CA $118
CA $137 total
Jul 20 - Jul 21
includes taxes & fees
8.4/10 Very Good! (305 reviews)
"Great. But the breakfast is bad because it’s all pork stuff. But hotel is nice"

Reviewed on Jul. 4, 2025

Sheraton Milwaukee Brookfield Hotel
See all 973 properties in Eagle
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 an Eagle vacation package cost?
Offering excellent value package deals from CA $739 on Expedia, you'll be pleasantly surprised at how much a vacation to Eagle costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Eagle?
The off-season is the best time to visit Eagle if you're hoping to keep costs down. Another tip for scoring cheap Eagle vacation packages? Try to avoid visiting during public holidays and any major events or festivals.
How many days is enough for Eagle?
With a well-organized itinerary, you can easily visit the top Eagle sights in a few days. But if you prefer to discover lesser-known spots or go on day tours, think about booking your Eagle vacation for longer.
Is it worth booking a vacation package to Eagle?
It's easy to see why an Eagle vacation is on the must-do list of many travellers. Top attractions like Old World Wisconsin are just the start of things to keep you busy here.
How to find the best Eagle package deals?
Landing a cheap Eagle package deal is a breeze with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your budget, add a couple of filters and browse what's available. You can tailor your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most wallet-friendly Eagle package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book an Eagle vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging flights and hotels individually. Better still, you can customize your Eagle getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Eagle?
If you have your Eagle vacation dates confirmed, book as soon as you can to bag some fantastic deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for travelling on a whim.
How to plan a trip to Eagle?

  1. Pick your dates: The things you want to do in Eagle and your favourite season can help you decide when to get away.
  2. Budget wisely: In addition to the price of your accommodations, you'll need to consider other expenses. These include food, flights and transportation. Also, put aside a little extra for unexpected costs that could arise during your trip to Eagle.
  3. Decide how long to go for: Now that you're up to speed on Eagle, you can figure out the ideal length of your break. Pull together a draft plan and give yourself enough time for all the things you want to do.
  4. Combine your airfare and accommodations: After you've nailed down your trip dates and duration, book the ideal Eagle vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.