Top 10 Budget-Friendly Winter Destinations in the Midwest

While everyone else waits for snow to clear, you'll score more affordable flights, discounted hotel rates and crowd-free attractions in some of the coolest cities in the country.

By: Katie Friedman

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Chicago, Illinois

Consider this one of the Midwest's best-kept secrets: winter is actually the perfect time to visit Chicago. Because the Windy City's off-season falls from early November to late March, many hip hotels like ACME and Freehand offer incredible promo deals this time of year, allowing you to stay downtown for a much smaller price tag. And while it might be too cold to dip your toes in Lake Michigan (unless you want to do the Polar Plunge), you can still hit The Beach Chicago, a free art installation at the Navy Pier, or ice skate at Maggie Daley Park for just $13 - $15. Better still, major attractions like the Skydeck have virtually no lines, so you can save on time as well.

Cleveland, Ohio

Waiting until the winter to visit Cleveland isn't such a bad idea, either. Once the summer crowds have cleared, you'll get the chance to experience the city's best sights and bites like a local. We suggest starting your day at the Cleveland Museum of Art, which offers free admission to the public, followed by a trip to the historic West Side Market, where you'll find over 100 food vendors. Don't foget to grab a seasonal donut and craft beer at the Insta-worthy Brewnuts or check out Cleveland's Winter Beerfest, where $45 will get you 25 sample drink tickets -- a total steal, IMO.

Detroit, Michigan

If there's one city that's meant to be seen this time of year, it's Detroit. Every November, Motor City pulls out all the stops with a huge skating rink, holiday markets and elaborate light displays that shine across town. You can lean into the season (and still stick to your budget) with a cup of hot chocolate and a game of Giant Jenga in the lodge at Cadillac Square, or by visiting during the Quicken Loans Winter Blast Weekends, a free event with food trucks, ice sculptures and slides. Arrive before Jan. 27 to catch Rainbow City Roller Rink, too; this whimiscal art installation won't cost you a single penny.

Grand Rapids, Michigan

About 2.5 hours north of Detroit, you'll find Grand Rapids, the second-largest city in the state and one that should definitely be on your list for 2019. Here, you'll walk across the iconic Blue Bridge, explore distinctive neighborhoods like Eastown and see Frank Lloyd Wright's Meyer May house -- all without spending a dime. And if you want to indulge a little? Well, let's just say that they call it "Beer City USA" for a reason. Grab a Brewsader Passport from the Welcome Center at the Grand Rapids Art Museum, visit 8 of the 40+ breweries in town and then trade your passport in for a free t-shirt.

Indianapolis, Indiana

As Indianapolis continues to become a major tourist destination, with Airbnb bookings up by 256% in 2018, it only makes sense to visit during the off-season. You'll still hit the highlights, like the Canal Walk and Monument Circle, but with the added bonus of being in town for Devour Indy and Winterfest. From Jan. 21 to Feb. 3, you can sip and savor your way through Indy's six Cultural Districts, as over 200 restaurants offer three-course meals at affordable prices, and then meet some of the best brewers in the country.

Milwaukee, Wisconsin

Speaking of beer, we've heard that Milwaukee is a dream destination for (21+) foodies this time of year. From now to April 13, you can enjoy free admission to the Milwaukee Winter Farmers Market, where over 50 different vendors sell baked goods, cider, jam and honey. Or, for just $15, you can check out Brewtanicals, a monthly series at The Boener Botanical Gardens where you'll meet with local brewers and sample their work. No trip to Milwaukee would be complete without a stop in Miller Valley, so spend the $10 on the guided tour and experience 155 years of brewing history in person.

Minneapolis, Minnesota

By now, we hope you know that there's more to Minneapolis than gray skies and snow. With diverse neighborhoods, food from around the world and a theater on almost every corner, this city is teeming with cultural activity -- especially during the winter months. In January alone, you can explore the Stillwater Ice Castles (tickets cost only $10), see the Winter Flower Show at the Como Zoo (for free), and of course, go ice skating in nearby St. Paul for a $4 rental. And that's just in addition to the city's other affordable attractions.

St. Louis, Missouri

Locals and seasoned travelers know that winter is a wonderful time to visit St. Louis. In addition to having most major attractions like the Gateway Arch and the City Museum to yourself, you'll be able to enjoy a variety of free activities like Winter Movie Nights at Ballpark Village or splurge on $30 tickets for your sweetheart at the annual Chocolate Wine Trail, which runs from Feb. 16 to 17.

Omaha, Nebraska

Home to the world's largest indoor desert and an expansive glass-enclosed garden, Omaha is exactly where you'll want to be this season. In fact, most activities in this Midwestern city are both reasonably priced and pedestrian-friendly. You can wander through the Gene Leahy Pedestrian Mall, a 10-acre park with lagoons and waterfalls, go for a stroll across the Bob Kerrey Pedestrian Bridge (and stick one foot in Nebraska & the other in Iowa), and take a free walking tour of Omaha's public art, which seems to stampede right through the city!

Wichita, Kansas

We're all about taking the road less traveled in 2019, which is why we're pointing you (and your wallet) towards Wichita, Kansas. Only here can you stand in awe of the great Keeper of the Plains, a 44-foot-tall steel sculpture that sits on the confluence of the Big and Little Arkansas rivers, and watch as the Ring of Fire illuminates it at sunset. Be sure to grab a cup of coffee from local favorite, Reverie, and then see the city and its many murals on foot for free.

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Top 10 Budget-Friendly Winter Destinations in the Midwest

Related To:

Shop This Look

Chicago, Illinois

Cleveland, Ohio

Detroit, Michigan

Grand Rapids, Michigan

Indianapolis, Indiana

Milwaukee, Wisconsin

Minneapolis, Minnesota

St. Louis, Missouri

Omaha, Nebraska

Wichita, Kansas

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