Winnebago Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

    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 Winnebago Vacation Deals

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

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Nice property, very walkable. Front desk was great. Bar area nice & welcome drink nice. Concierge was not around. Got suite with 2 full baths which was awesome with teens. Great stay overall!

Reviewed on Jul. 12, 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
Hotel staff and room were awesome..bed very comfortable. Coffee shop was great had great fast breakfast options. Had Miss Rickie's one day was really great food. Only complaint would be the rooftop bar evening clientele...did not feel comfortable and they were loud and raucous.

Reviewed on Jul. 8, 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 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
I didn’t like the staff insinuating that I couldn’t afford a bottle of Dom. I didn’t like the 3 calls to my room to make sure I understood what the price was. I didn’t like how Brandy told me the reason for doubting my ability to pay for a $700 bottle of champagne was because of what my “profile” said about me. I would love to see this profile they had on me. I did not appreciate being embarrassed in front of my wife. We spent close to 10K at this place for the 7 days we spent there. We chose to stay at Trump Intl in Chicago because we can afford to do so. I understood before checking in that it would be very expensive. I did not know that a profile would be built about me and I would be judged by the staff according to it. I will never stay at a Trump hotel again. There are too many hotels to chose from to have to deal with this kind of treatment.

Reviewed on Jul. 12, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
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

Renaissance Chicago O'Hare Suites Hotel

Renaissance Chicago O'Hare Suites Hotel

4 out of 5
O'Hare
Save 100% on your flight
per person
Oct 5 - Oct 11
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.4/10 Very Good! (1,007 reviews)
Great for a one night stay! The hot tub / pool area was really nice to use.

Reviewed on Jul. 9, 2025

Ready to book your vacation to Winnebago?

 

Choose your dates

Winnebago Hotel Deals

Baymont by Wyndham Rockford
Baymont by Wyndham Rockford
3 out of 5
662 N Lyford Rd, Rockford, IL
Fully refundableReserve now, pay when you stay
The price is CA $95 per night from Aug 3 to Aug 4
CA $95
CA $109 total
Aug 3 - Aug 4
includes taxes & fees
9/10 Wonderful! (1,223 reviews)
"Older but well kept property."

Reviewed on Jul. 10, 2025

Baymont by Wyndham Rockford
AmericInn by Wyndham Beloit
AmericInn by Wyndham Beloit
2 out of 5
2790 Milwaukee Rd, Beloit, WI
Fully refundableReserve now, pay when you stay
The price is CA $134 per night from Jul 14 to Jul 15
CA $134
CA $152 total
Jul 14 - Jul 15
includes taxes & fees
8.6/10 Excellent! (46 reviews)
"Like the area located close to pearl lake, food options, rooms clean but it can use some upgrade in the bathroom other than greattt."

Reviewed on Jul. 5, 2025

AmericInn by Wyndham Beloit
Econo Lodge
Econo Lodge
2 out of 5
7712 Potawatomi Trail, Rockford, IL
Fully refundableReserve now, pay when you stay
The price is CA $80 per night from Jul 20 to Jul 21
CA $80
CA $92 total
Jul 20 - Jul 21
includes taxes & fees
8.2/10 Very Good! (865 reviews)
"In and out on my way back from vacation, decent enough to spend the night"

Reviewed on Jul. 10, 2025

Econo Lodge
See all 210 properties in Winnebago
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 Winnebago vacation package cost?
You can snap up a vacation package to this destination from CA $749 on Expedia. But how much your vacation to Winnebago costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Winnebago?
Plan your trip for the off-season and you're likely to find cheap Winnebago vacation packages. Remember that school vacation periods and major festivals and events can impact prices, so do some research before you go.
How many days is enough for Winnebago?
The ideal duration of your Winnebago vacation depends on what you'd like to see and do. Typically, a handful of days to a week will give you plenty of time to hit all the main sights and explore some hidden spots along the way.
How to find the best Winnebago package deals?
Use Expedia's handy filters to help you find some terrific Winnebago package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Winnebago package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Winnebago vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component individually. And you'll still get the flexibility to create a tailored Winnebago vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Winnebago?
Land amazing discounts by reserving your flights early with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu Winnebago getaway.
How to plan a trip to Winnebago?

  1. Pick your dates: The things you'd like to do in Winnebago and your preferred season will help you decide when to get away.
  2. Figure out your budget: Make sure you have enough money to cover everything from meals and transportation to activities and airfares. Your hotel will likely be the largest expense during your trip to Winnebago.
  3. Work out your trip length: Consider how long you'd like to spend discovering Winnebago. Plan your days so you can get to all the activities and attractions you're interested in at a comfortable pace.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to find a Winnebago 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.