5 Long Weekend Vacations in the Midwest for Less Than $500

If you need a long weekend and you’re in the heartland, you’re in luck. The Midwest is filled with charming, fun locations to spend a few days — and not go broke while doing so. This area has it all: bustling cities, quaint lakeside retreats and so much more. GOBankingRates spoke with travel experts to get the inside scoop on five fantastic spots where you can stretch your dollar and save money while also maximizing your fun in the Midwest.

Here are five long weekend vacations in the Midwest for less than $500.

Also see 10 things to consider before taking a vacation.

Think Chicago’s too pricey? Think again. Michael Santiago of RetireGuide.com said you can potentially explore the Windy City for under $500 if you play your cards right.

“Consider staying at budget-friendly hotels or an Airbnb in well-connected neighborhoods like Lincoln Park or Wicker Park,” Santiago said. “A room can cost you around $100 per night, though you can find options as low as $79.”

Once you’re settled, the city’s your oyster. “Use free or low-cost walking tours to take in the city’s architecture,” Santiago said. “You can also visit Millennium Park, the Art Institute of Chicago (free for Illinois residents on specific days), walk around Navy Pier, visit Willis Tower or take a bike ride along Lakefront Trail.”

And let’s not forget the food. “Chicago is home to many ethnic neighborhoods offering quality food at affordable prices,” Santiago said. “And if you’re up for it, try the deep-dish pizza.”

For a perfect blend of culture and nature, set your sights on Saugatuck. Janice Moskoff of Gather and Go Travel raved about this Michigan beach town.

“Just under a three-hour drive from Chicago and roughly the same from Detroit, discover the artist-haven and west coast Michigan beach town of Saugatuck,” Moskoff said. “Situated on the Kalamazoo River opposite the dune headland that separates it from Lake Michigan, you will find more to do than you can fit into a long weekend.”

Moskoff suggested affordable activities like kayaking, paddleboarding and hiking. “Hike the Saugatuck Natural Harbor Area trails, including the path to award-winning Oval Beach, parking in the lot at Mt. Baldhead Park,” she recommended.

To keep costs down, Moskoff advised staying nearby. “Stay in the nearby towns of Douglas or Fennville to keep lodging costs down, especially since rentals and inns in Saugatuck can run pricey,” she said.

Ronee Uyeshiro, founder of The Hotel Shortlist added, “For a charming and LGBTQ+-friendly getaway less than an hour from Grand Rapids, head to ‘The Art Coast of Michigan,’ located on the lake’s eastern shore. Stroll the art galleries, take to the water on a double-decker paddlewheel boat, the Star of Saugatuck or spend some time out in nature at Saugatuck Dunes State Park.”

Madison offers a quintessential Midwest experience without breaking the bank. Santiago broke it down: “Booking a budget hotel or Airbnb near downtown can run about $90 per night, but you can find rooms for as low as $54 per night.”

Once you’re there, the city’s full of affordable attractions. “The Wisconsin State Capitol offers free tours, and you can also explore Olbrich Botanical Gardens, tour the University of Wisconsin-Madison campus or visit one of the local farmers’ markets in Capitol Square,” Santiago said. “Additionally, Lake Mendota offers kayak and paddleboard rentals.”

Food lovers, rejoice. “When you’re ready to dine out, Madison boasts many affordable farm-to-table restaurants, food trucks and local cafes,” Santiago added.

The Twin Cities offer big-city amenities at small-town prices. “Consider staying in the vibrant neighborhoods of Uptown Minneapolis or near the Mississippi River in St. Paul. Average prices are around $90 per night, but you can find rooms for as little as $52,” Santiago said.

The cities are packed with affordable attractions. “The city offers many sites to explore, such as the Minneapolis Sculpture Garden, the Conservatory in St. Paul, the Stone Arch Bridge, Como Park Zoo and Conservatory (free) and the Walker Art Center (free on specific days),” Santiago explained.

And don’t forget the food scene. “Affordable dining consists of local restaurants and ethnic cuisine,” Santiago said.

For outdoor enthusiasts and history buffs, Echo Wang, CEO and founder of Cool Travel Vibes, recommended southern Illinois. “Nature lovers will adore the stunning hikes in Garden of the Gods and the surrounding areas, all without breaking the bank. Free camping options are available too!” Wang said.

It’s also a great place to bring your whole crew. “For family fun, St. Louis’ City Museum is a must-see,” Wang added. “Outdoor enthusiasts can explore Shawnee National Forest, cast a line in numerous fishing spots or simply soak up the natural beauty.”

Of course, this area is all about the food too. “Don’t miss out on the local flavor with incredible BBQ at 17 Street and Pat’s in Murphysboro, or indulge in delicious pizza at Quatro’s,” Wang said.