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Your Road Trip Guide for the Chicago to Wauwatosa Drive

Plate full of deep-fried cheese curds with hands pulling one apart.

Pack your bags — you’re heading to Wauwatosa. Whether you’re making the trip with friends or planning for a family-fun weekend, we’ve mapped out the perfect road trip from Chicago to the Milwaukee area that includes our charming city.

How Far is Chicago from Wauwatosa?

If you’re making the drive up north, plan for approximately an hour and a half to two hours (without traffic) on the road when you take I-90 W to 1-94. Then, follow I-94 to I-41 right into Tosa.

If you’re looking to avoid traffic and just go along for the ride, the Amtrack Hiawatha line from Chicago to Milwaukee is an easy two to two and a half hours. Simply jump on at Chicago Union Station and ride to Milwaukee Intermodal Station. 

Discover all the places to make a pitstop along your journey (by car), as well as must-visit places to go when you get here — we can’t wait to welcome you to Wauwatosa!


En Route to Tosa

The Brat Stop

Location: Kenosha, WI | Minutes from Tosa: ~ 40 minutes

Along the West side of I-94, you’ll find the Brat Stop, which is World Famous for all things brat and cheese related. Referred to as the “50-yard line” by owner and founder, Gerald Rasmussen, this American restaurant and cheese shop is located only 5 minutes from the Wisconsin/Illinois border — perfect for whichever team you root for. Find an impressive selection of bratwursts, delectable sandwich options, and plenty of pizza.

Mars Cheese Castle

Location: Kenosha, WI | Minutes from Tosa: ~ 38 minutes

Located just six minutes closer to Tosa from the Brat Stop, Mars Cheese Castle is another Wisconsin staple. You won’t be able to miss the prominent white castle landmark on the West side of the road. Stop in for cheese (of course!) and a bakery with an assortment of meats and spreads. Plus, this is where Food Network’s Jeff Mauro of Sandwich King found the perfect provolone and aged cheddar for his very own grilled cheese sandwich!

Apple Holler

Location: Sturtevant, WIc | Minutes from Tosa: ~ 35 minutes

Keep driving another seven minutes north to Apple Holler, a family farm, bakery, farm-to-table cafe, country store, and seasonal you-pick orchard for apples, peaches, pears, and pumpkins. Their restaurant’s ever-changing menu features fresh ingredients, so you can taste the family farm’s seasonal produce. They also have an abundance of family-fun activities throughout the year including, orchard and farm tours, children’s shows, hay rides, sleigh rides, barnyard animals, and outdoor play areas. 

Plus, don’t forget to pick up a pack or two of Spotted Cow beer — IYKYK. 

7 Mile Fair 

Location: Caledonia, WI | Minutes from Tosa: ~ 25 minutes

Continue your road trip 12 miles north of Apple Holler to 7 Mile Fair. This indoor/outdoor flea market features local vendors and bargain shopping with family fun every weekend of the year. Access hundreds of vendors spread across 40 acres for a wide choice of locally grown products and new, gently used items. The indoor market is open every weekend from 9AM-5PM, and the outdoor market is officially open the first full weekend of April through the end of October from 9AM-5PM (including Memorial Day and Labor Day). 


“En Wauwatosa”

Catch A Game

Whichever team you root for, don’t miss the chance to check off American Family Field (located just five minutes from Tosa!) and Fiserv Forum from your stadium or arena bucket list. Perfect for family-fun outings, watch the Milwaukee Brewers play or catch the 2x NBA Champion Milwaukee Bucks game.

Feeling inspired to get active? Wisconsin’s first and only football bowling bar, 1st & Bowl, is exclusive to Wauwatosa and fuses sports and games for the ultimate indoor gaming experience. Giving off a ‘cornhole’ vibe, it’s the perfect laid-back approach to sports. Plus, their bar is set up in the middle of the warehouse facility, making it a super social scene, too!

Devour Deep-Fried Cheese Curds

It’s all about that cheese pull here in Wauwatosa, and Tosa’s local restaurants have it going on. Scattered throughout our five dynamic districts, the deep-fried curds from Buckatabon, Leff’s Lucky Town, Café Hollander, Crafty Cow, and Golden Nest Pancakes will have you running (or road tripping!) back to Tosa in no time.

Munch on Macarons

Unofficially known for the best macarons in Wisconsin, Wauwatosa’s local bakeries know how to make one mean macaron. 

Stop into Le Rêve Patisserie & Cafe for a classic taste of this French delicacy with raspberry, pistachio, lemon, and hazelnut macaron flavors. Also located in Tosa Village, Black Twig Bakery offers seasonal macaron flavors — check out their monthly menu for the latest and greatest offerings. Plus, Rocket Baby Bakery in East Tosa offers an assorted macaron two-pack, which serves as the perfect gift to bring home to a friend or the perfect little treat for you!

Bonus: Looking for more planning inspiration for your upcoming trip? Dive into where to stay, what to do, and where to go if you only have 72 hours to spend in Wauwatosa.

Discover Wauwatosa wants to ensure you have a safe and healthy travel experience. Learn more about where to stay, where to eat, and things to do while you’re here in Wauwatosa. 

Due to the coronavirus pandemic, please check the local hotel and travel restrictions and retail and restaurant hours/menus before you go. 

Header image courtesy of @buckatabon.