Eagle Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
Baymont by Wyndham Glenview
Price was CA $768, price is now CA $557 per person
CA $557
per person
Jul 30 - Aug 2
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
7.6/10 Good! (1,004 reviews)
Breakfast was there but not a lot
Look at moving in individuals using it as a home
Good location though nice area around the place
Reviewed on May 9, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,355, price is now CA $1,579 per person
CA $1,579
per person
Jul 30 - Aug 2
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
If you plan on staying in this hotel by all means the view is great, but if you plan on moving your vehicle at all the hotel does not validate In-N-Out parking. You have to pay every time you want to leave and come back. Unlike the normal hotel, La Quinta downtown Chicago validate parking yes it’s $70 but you can drive in and out as many times as you want during your stay. Unlike this hotel.
Reviewed on May 8, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,235, price is now CA $899 per person
CA $899
per person
Aug 1 - Aug 3
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,137 reviews)
Keep an eye that nothing is added from the minibar but great property and can't wait to stay again!
Reviewed on May 5, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,146, price is now CA $1,596 per person
CA $1,596
per person
Jun 25 - Jun 28
found 19 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (1,851 reviews)
Horrible, horrible housekeeping staff many times I had to have head of housekeeping come and monitor
Very disappointing
Reviewed on May 10, 2026
Eagle Hotel Deals
Harbor Shores on Lake Geneva
300 Wrigley Dr Lake Geneva WI
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from May 12 to May 13
CA $135
CA $184 total
May 12 - May 13
includes taxes & fees
9.2/10 Wonderful! (1,341 reviews)
Too early for outdoor pool. Front desk person at check in was not very friendly or helpful. Made us feel less than welcome. Didn’t seem interested in answering any questions. We had a lakeside room but it overlooked the roof and was not an attractive sight with all the mess on it. Plus they were ...
Reviewed on May 9, 2026
Sheraton Milwaukee Brookfield Hotel
375 S Moorland Rd Brookfield WI
Fully refundableReserve now, pay when you stay
The price is CA $141 per night from May 24 to May 25
CA $141
CA $163 total
May 24 - May 25
includes taxes & fees
8.4/10 Very Good! (786 reviews)
We had an issue when getting into our room. The front desk handled it immediately and even gave us free breakfast the next morning. All staff was very friendly! We went to dinner that night and the staff again was very friendly but the food was NOT good. We ordered a "smash" burger... it was just ...
Reviewed on May 10, 2026
Timber Ridge Lodge and Waterpark
7020 Grand Geneva Way Lake Geneva WI
Fully refundableReserve now, pay when you stay
The price is CA $207 per night from May 14 to May 15
CA $207
CA $284 total
May 14 - May 15
includes taxes & fees
8.6/10 Excellent! (3,254 reviews)
Very nice accommodations
Reviewed on May 4, 2026
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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
