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Chicago To Milwaukee Road Trip Guide

Some people chose to book flights to Chicago before Newcastle's preseason match in Milwaukee. Here are some things to do and places to eat while in Chicago and along the way to Milwaukee.

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I have not been this excited about a preseason game in any sport my entire life. The fact that Newcastle United are playing within a stone's throw from where I live is something I was hoping for. I even pleaded my case a couple months ago on why it is a great place to play a match or three. My wish was granted, and I am excited to meet Newcastle fans from near and far and enjoy the match together.

I have spoken with a few fans already about this match who are traveling from across the country. Many of you elected to book your flights into Chicago and rent a car for the short drive to Milwaukee instead of the more expensive direct flight there. Others are road tripping to the match (I'm looking at you Toronto Toon Army) and will stop in Chicago for a meal or two before heading to Milwaukee. Regardless of your travel choices, you will still have to drive between Chicago and Milwaukee. As one of the admins of Toon Army Chicago, I feel like I would be doing all of you a disservice if some recommendations were not given along the way. The Chicago-Milwaukee trip is one of my favorite short day or weekend trips to visit friends, make a beer run for New Glarus brews, or take in a baseball game at Miller Park. My recommendations will be for places to see and stop while in Chicago and driving to your destination.

While You Are In Chicago


Chicago Skyline

A view of Soldier Field and the Chicago skyline along Lake Michigan

If you have time to take in some touristy things while in Chicago, I strongly recommend doing it. There's the bean in Millennium Park, a popular place for mirrored selfies and other photographic exercises. You have one of the best-looking and most diverse skylines in the world to view. You can take an architectural boat tour, and two of the tallest have public observation decks. The Sears Tower (I am a Chicagoan and refuse to use the W word) has their Skydeck, complete with glass cube you can venture on and view the city below. There is an observation deck at the Hancock Tower with a new tilting mechanism so you can view the city on your stomach.

Both will set you back around $20 for entry, and I can't whole-heartedly recommend either one. Instead, put on somewhat nicer clothes (a polo and jeans will suffice) and head to the Signature Room Lounge at the Hancock Tower. Their bartenders are consistently rated among the best in the city, and their seasonal non-alcoholic options (smoothies in the spring/summer, hot drinks in the winter) are also very tasty. For that same $20 price, you get a drink, a seat, and an equally stunning view. I am recently engaged, and this is where I proposed. A side note from my fiancee: If you are a female, be sure to use the restroom. I've only seen her pictures, but she claims it is the best view of the city. us guys get the short end of the stick and only see a generic men's room.

Signature Room Sunset

The Signature Room Lounge at sunset. Photo credit Cindy Kelley

If architecture and heights are not your thing, you can enjoy other activities. There are beaches along Lake Michigan, and they will be full of people sunbathing, playing beach volleyball, or they will be along the bike path getting in a good workout. You can rent bikes at one of the bike stands or use the city of Chicago's Divvy bike share system. Chicago is becoming more and more bike friendly, and you can explore most of the city on one of the bike lanes or bike paths, including a recommissioned L track overpass called The 606. It is a very similar to New York City's High Line.

American Gothic

A couple viewing Grant Wood's American Gothic at the Art Institute Chicago. Photo credit Flikr user Phil Roeder

If family attractions are what you seek, Chicago is also home to world-class museums. You can travel back in time to the age of dinosaurs and Vikings alike with a trip to the Field Museum or explore the universe at the Adler Planetarium, the country's first planetarium. You can explore many scientific phenomena, hands-on exhibits, and the history of inventions that make modern society work at the Museum of Science and Industry. You can view priceless works of art, sculpture, and photography at both of Chicago's world class art museums: The Art Institute and the Museum of Contemporary Art. Another option is the Lincoln Park Zoo, one of the few remaining zoos that is free to the public.

These are all amazing places to go that people travel from all over the world to visit. Do yourself and your wallet a favor and avoid Navy Pier at all costs.

There will be plenty of sports action to take in the weekend before, too! The Cubs host crosstown rivals the White Sox in their last games before the All-Star Break. If footy and footy only is on your brain from when you land, the Chicago Fire host former Newcastle striker Obafemi Martins as the Seattle Sounders invade Toyota Park on Saturday, July 11. Oba will be seeking redemption after his trip to Chicago last year. He scored two goals and got sent off in the first half in their 3-2 defeat of the Fire.

Toyota Park

A picture of me repping the Toon at a Fire match. Photo credit: Cindy Kelley

In traditional Chicago summer fashion, street festivals and concerts will be taking place at the city's multiple venues. One of Chicago's longest running and most popular festivals the Taste Of Chicago will be taking place in Grant Park. The city's diverse food offerings will be on display, and live music will also be abundance in Chicago's largest park. Concerts galore are taking place all over Chicagoland that weekend. A wide variety of musical acts are all in Chicago the weekend before, including Nickelback, 311, Meghan Trainor, Aretha Franklin, and a screening of Fantasia and Fantasia 2000 with music from the Chicago Symphony Orcherstra is also taking place. Tickets for most of these shows can be found on Ticketmaster.

Food & Drink

Lou Malnati's Pizza

A pair of Lou Malnati's pizzas waiting to be served. Photo credit Kent Wang

If you are not into architecture, street festivals, music, or beaches, I think I can speak your language. In my opinion, I think Chicago is one of the most diverse and creative restaurant scenes in the country, if not the world. You can get anything from a high quality steak to any combination of fusion dishes to one of the most fundamentally solid burgers or pizzas you will ever find.

If you want to stick with the basic classic Chicago-style dishes, your three options are: Italian beef, deep dish pizza, and Chicago-style hot dogs. All three of these are available in the city and suburbs. While you're in the city, any independent fast food place will do a solid Chicago-style hot dog. Angry words, violence, and/or ejection can occur if you ask for ketchup on them. Many people from out of town associate Portillo's with their haven for Chicago-style hot dogs. They are always a safe bet in this category.

A lot of people also associate Portillo's with quality Italian beef sandwiches, and they are not wrong. They make a killer beef sandwich, and their beef and Italian sausage combo is also a home run. If you're in the city limits, I suggest trying Al's Beef or Mr. Beef, instead. Al's is known for great beef and amazing fries. Mr. Beef is another Italian beef staple, and it is a personal favorite of Jay Leno's. If you order these correctly--dipped with mozzarella cheese and peppers--they can be a messy handful. Do yourself a favor and eat them at the restaurant.

Depending on who you talk to, you will get one of two recommendations on what deep dish pizza joint to visit: Lou Malnati's or Girodano's. People's opinions on these two run as deep and passionate as people's allegiance to the White Sox or Cubs. I fall in both the White Sox and Lou Malnati's category. A lot of friends from out of town rave about how great Girodano's is, and most of the time they are blown away when I take them to Lou Malnati's. If you can't get to one of Lou's many locations, I suggest Gino's East or Pequod's instead. These are both great options.

If you can say "been there, done that" to traditional Chicago fare, level two of quintessential Chicago eating involve individual places. For the best done quick-order burger (and star of the classic SNL sketch), order yourself a cheezborger at the Billy Goat, chips no fries, Coke no Pepsi. Level 2 of Chicago food also includes legendary German restaurant the Berghoff. In addition to great German food and their own beers, they are holders of Chicago's first liquor license after prohibition ended. Future Chicago culinary legends Kuma's Corner and Au Chevalrated best burger by Bon Appetit magazine, are also places that you will not leave hungry nor disappointed. You can also check out places featured on shows like Diners, Drive-Ins, and Dives, or you can view home picked places from WGN TV's Chicago's Best. I have been to many places featured on both, and you cannot go wrong with any of them.

If locally sourced booze is what you seek, you can check out one of Chicago's breweries. Despite being owned by Anheuser-Busch, Goose Island still brews many beers in Chicago. Pick the ones with the Chicago flag next to them, and you're enjoying a Chi-town brew. Other local powerhouses include Revolution Brewing and the new Lagunitas brewery, an expansion of their west coast operation. They may be in Indiana, but Three Floyd's beers can be found in many liquor stores and bars all over the city. You can also enjoy locally made wine at City Winery and locally made craft spirits at the Chicago Distilling Company.

Driving To Milwaukee

At this time of year, there are three things you can count on when driving in and around Chicago: Traffic, Tolls, and road construction. Two of the three are unavoidable, the avoidable thing being traffic (mostly). If you are flying into O'Hare, the easiest route is to take I-294 North toward Wisconsin. It passes just outside O'Hare, and it is easy to get to. For those flying into Midway, your best route is to take I-55 north into Chicago to I-90/94 west. When 90 and 94 separate, keep right at the fork to stay on I-94. Interstates 94 and 294 become one highway north of the city, and this will take you into Wisconsin. If at all possible, I highly recommend leaving between 9AM-3PM. Otherwise, expect your drive to look something like this.

Chicago Traffic

Photo Credit: Quinn Dombrowski on Flickr

Regardless of your route, you can expect to pay tolls. If your home state uses the EZ Pass system, bring your transponder. It will work on Illinois tollways. If you do not have a transponder, bring cash and change. Each route will have 1-2 tolls, including a final one just shy of the Illinois/Wisconsin border.


If you are looking for food along the way, your options unique to Illinois and Wisconsin are somewhat few and far between. If you crave Chicago native foods, there are Lou Malnati's and Portillo's within a 15 minute drive of O'Hare and a Portillo's is within 10 minutes of Midway. Locations of both Portillo's and Lou Malnati's are peppered along Interstates 94 & 294 on your way north. A favorite of both Diners, Drive-Ins, and Dives and Chicago's Best, Paradise Pup, is also a close drive from O'Hare. If you get there early in the afternoon, I strongly recommend this being your stop. Their burgers are incredible, especially with the Merkt cheddar spread they use for cheese.

If you can wait until you cross into Wisconsin, you will also not be disappointed. A favorite of both my parents and myself, The Brat Stop in Kenosha, is just across the border. If Portillo's is quintessential Chicago food, The Brat Stop is the same for Wisconsin. Their bratwurst and cheddarwurst are hands down the best I have ever had anywhere. The buns they use in addition to the high quality sausage are a combination so good, I dare you to find a better one. Their fried cheese curds are an especially amazing appetizer, and they pair well with the many beers they have on tap. This is the first time you can experience the greatness that is New Glarus Brewery's Spotted Cow, and you cannot pass up trying that while in Wisconsin.

Brat Stop

The Brat Stop in Kenosha, WI. Photo credit Flickr user Kevin Tao

A short trip up the road is a popular stop for tourists and locals alike, the Mars Cheese Castle. Home to a wide variety of locally made cheeses, meats, and baked goods, they are a great place to experience and purchase a slice (or tub) of Wisconsin. If you like what you find there, you can order more online and have it shipped to you.


A lot of the drive between Chicago and Milwaukee is urban sprawl. Along the way there are some fun places to enjoy shopping, thrills, and an immature giggle along your way up north.

If you forget anything when you packed, or if you (or your significant other) get the urge to bargain hunt, you are in luck. Gurnee Mills, one of the nation's largest shopping mall, is conveniently along the route to Milwaukee. Home to over 200 stores, it is a place one can get lost in while shopping. Other big box stores like Dick's Sporting Goods also pepper the landscape surrounding the mega shopping center.

Great America

An aerial view of Six Flags Great America. Photo credit Flickr user David B. Gleason

If you elect not to shop, one of the nation's top theme parks is mere miles away. Six Flags Great America, home to some of the nation's elite roller coasters, is on the other side of I-94. It is home to top wooden coasters like American Eagle, Viper, and the tallest and steepest Goliath. It is also home to comic book themed rides for both Batman and Superman, Vertical Velocity, and the mega drop and speed coaster Raging Bull. There is also a full outdoor water park, complete with water coasters like Mega Wedgie, Vortex and Typhoon, and the Dive Bomber. There is also a second indoor water park in Gurnee, Key Lime Cove, in case the weather is not suitable for rollercoasters or an outdoor water park.

Bong Recreation Area

The Bong Recreation Area sign, circa 1960. Photo courtesy of Wisconsin Dept. of Natural Resources

For those experiencing a taste of nature and an immature giggle, the Bong Recreation Area is for you. No, this is not a pothead's safe haven in Wisconsin, but the name, like Climax, MI, is highly amusing. It is a wildlife area with abundant trails for biking, hiking, dirt bike and ATV riding, and plenty of water for swimming and fishing. Before you ask or visit their website, yes, they do sell t-shirts and other merchandise. From here on in, you are within 45 miles of Milwaukee and your final destination.

If any of you have any other places to throw into the mix, I am willing to hear your opinions. I am always looking for great places to enjoy and share with others. Enjoy your trip to Milwaukee, and I will see you there!