Escape Wisconsin: Hot Snowbird Migration Destinations

Hiking trails on mountain

Where to go when you need a break from winter.

For those of us who call Northeast Wisconsin home, the following items conjure some strong feelings.

  • Ice scraper
  • Snow shovel
  • Remote starter
  • Winter boots

When Wisconsin winter is just a little too much, it’s time to spread your wings and fly somewhere warm and leave winter woes (and that dang ice scraper) behind.

Here’s where on-trend, on-budget Wisconsinites are going:

1. Davenport, Florida | Member Advisor Rating: $

Davenport golf club via Chad Sparkes

(Photo at a Davenport golf club, via Chad Sparkes – Flickr)

If your youngest son or daughter is set on going back to Disney, but you’re not willing to put up with Orlando traffic and crowds, stay in nearby Davenport, Florida. TripAdvisor was ahead of the Davenport trend in saying, “people are realizing this small town has its own delightful attractions. Hit Lake Kissimmee State Park for outdoor recreation, the Highlands Reserve Golf Club for polishing off your nine iron, or head downtown for great food and better shopping.”

Lodging in Davenport comes at small-town prices, too—check out this awesome 5-bed, 5-bath VRBO listed at $199/night! Roundtrip tickets from Chicago airports to Orlando (MCO) can be found in the $130-$200 range.

2. Dallas, Texas | Member Advisor Rating: $

dallas texas getaway

(Photo via Eric Borja, Flickr)

USA Today lays out Dallas’ big selling points: the weather hovers in the 50s and 60s in winter, and the city is dense with free attractions (Dallas Arboretum & Botanical Gardens), museums (DMA), and picturesque, highly walkable neighborhoods.

Roundtrip seats from Milwaukee to Dallas can be as cheap as $160, and a quadruple room (two king beds) in a central hotel will run you about $260 a night.

3. Sanibel Island, Florida | Member Advisor Rating: $$

florida snowbirds

(Photo via Freebird, Flickr)

Another key destination for the Sunshine State, Sanibel Island is ranked #6 in Winter Family Vacations on U.S. News & World Report’s list for several good reasons. Sanibel visitors will enjoy sandy shores stocked with seashells (say that five times fast), fresh seafood, and temps in the mid-70s.

A “Very Good” hotel booking for a family of four in January 2018 runs as low as $206/night. Flights from Milwaukee to Fort Myers (20 minutes from Sanibel) will cost you about $250/ticket.

4. Gulf Shores, Alabama | Member Advisor Rating: $$

(Photo via John Tuggle, Flickr)

“Sugar-white-sand beaches, a culinary scene rivaling New Orleans’, a vibrant shopping district”—Architectural Digest lists some of the perks of this underrated beach town, and there are many more. Gulf Shores might be the best vacation spot on the Gulf Coast for sun-loving families.

Seats (roundtrip) from Chicago to Pensacola (this airport is about an hour drive from Gulf Shores) will cost about $300, and you can get your hands on a striking VRBO house rated “Exceptional” that sleeps eight for $159/night.

5. Scottsdale, Arizona | Member Advisor Rating: $$$

scottsdale arizona

(Photo via Dru Bloomfield, Flickr)

Scottsdale, Arizona’s fifth-largest city, is known internationally for its art galleries, and is host to countless souvenir shops, interior design studios, and an active artists’ community. If shopping is your thing, Scottsdale’s Fifth Avenue is the go-to for high-end goods and Native American jewelry and crafts. When you’re not shopping, Scottsdale is the place to play a few rounds of golf or catch some rays by the pool.

A roundtrip fare from Milwaukee to Phoenix (Scottsdale is a 22-minute drive from Phoenix) ranges from $100 to over $500, depending on what you prefer. Hotel prices for a family of four will be a little pricier, hovering around the $300 mark.

6. Madeira, Portugal | Member Advisor Rating: $$$$


(Photo via Willfried Wurch, Flickr)

Because it’s slightly cooler than more mainstream Mediterranean destinations, Madeira is an affordable choice for budget-conscious travelers. This semitropical four-island archipelago (and country of origin of the wine with the same name) offers breathtaking hiking trails and gourmet fare for foodies of all ages. This is the most expensive location on our list, but it’s relatively inexpensive compared to other international locales.

Roundtrip flights hover around the $1,000 mark from Chicago O’Hare (ORD) to Madeira (FNC), but 4-star hotels can be as low as $100 per night if you keep your eyes peeled for deals.

Now that you’re at the end of this list, would you rather:

  • Dust off your flip flops and bathing suit
  • Get your snow blower serviced

Yeah, we thought so. Set up a vacation savings account or get help financing a winter getaway for you and your family with one of our Member Advisors. They’re on call and ready to get you set up with your very own U Choose loan. Want to explore other financing options? Check out our personal services offerings.

Cover photo credit: Willfried Wurch, Flickr

Flight price ballparks were calculated using, booking for two adults, two children (ages 9 and 13), with departure on 1/13/2018 and return on 1/20/2018. Hotel prices were estimated using TripAdvisor,, and for two adults, two children (ages 9 and 13), with departure on 1/13/2018 and return on 1/20/2018. Prices are not final or representative of prices from all sources. Pricing information is provided as a rough estimate for research purposes only and is subject to change.
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