Travel like Too Fit: Chicago

Over the course of this past year, we have covered some ground in the territorial United States, to say the least. The list of cities that have played host to our shenanigans includes:

St. Louis, Denver, Orlando, Portland, Atlanta, Chicago, Des Moines, Kansas City, and of course all over our home state of Texas. This list is ever-growing as we speak. You should see the calendar! (Louisville, Tulsa, Little Rock, Pasadena, Canada, and back to Orlando, just to name a few).

Most of these trips have a business purpose, but we find time to seek out adventure and inundate ourselves in the city life by finding local eateries and off the beating path attractions.

In these posts, Travel Like Too Fit, we will unfold for you the places we stayed, where we filled our gullets, and what escapades we attempted. We hope you find them both entertaining and useful!


Where we stayed:

The Chicago Athletic Association

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During our travels, it’s a rarity to have a hotel and itinerary all mapped out; a Type-A personality’s worst nightmare. Most of the time we utilize Hotel Tonight or to snag a last minute deal. While we win most of the time, it can come back to bite you. We have a few stories and a few scars on that note. Don’t ask.

However, The Chicago Athletic Association was definitely a win! As you enter the lobby of the hotel, it feels like you stepped into early 20th century America. With all natural lighting, a room built from rich, dark wood, with the aroma of leather, three fireplaces, and a conference table that operates as a co-working space. It as if you stumbled on the set of Mad Men. You’re expecting Don Draper to appear with a drink in hand at any moment.

As you make your way up the marble staircase, the remnants of the Chicago Athletic Association pool awaits you. The room is supported by beautiful, marble pillars stretching from the floor of the room to the ceiling. By far the most intriguing aspect of this place, the floor of the pool was left in place and now serves as the Hotel conference room. Surrounded by pictures of the pool in its heyday, you can gather a real sense of what the place looked like when operational.

They even decorated the elevators with the original fencing room floor! How’s that for interior design?

Now, the hotel room leaves the lasting impression. It’s difficult to distinguish from one hotel to another if the room is adequate, but a nasty hotel room can easily ruin a visit. The rooms here are undeniably unique and mesh with the athletic theme of the hotel. As footstools, you will find pommel horses (a leg swing is harder than it looks, by the way). Stepping out of the shower in gray, cotton bath robes make you look fight-ready; preparing to go toe-to-toe with Muhammed Ali. Complete with a simple work desk and an old-fashioned mini bar, you can choose whether to work or play.
Lastly, we come to the hotel gym. Let’s be honest, the modern hotel gym needs a serious make-over. On the contrary, The Chicago Athletic Association remained true to its roots and hosts a state of the art facility. We were lucky enough to have the gym to ourselves; so needless to say, we cranked the music and worked out like no one there had since 1920!

Chicago Athletic Association

Chicago Athletic Assoication

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Where we ate: 

Wildberry Pancakes and Café

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First and foremost, you should know that I am an avid breakfast fanatic. I literally attempt to turn every meal into breakfast. Don’t be surprised when we go for tacos and I consume only bacon and eggs, or when I suggest Cracker Barrel for dinner. I consider myself a breakfast connoisseur of sorts, so naturally, when we arrived in Chicago, brunch was on the menu.

I’m not exaggerating when I say Wildberry Cafe has the most unique and creative breakfast menu I’ve ever seen, not to mention the tastiest. May I suggest the Corned Beef Benny Benedict with a Fig and Walnut pancake to boot. You’ll be in food coma heaven afterward, but an arrival in the Windy City is binge-worthy.


Do-Rite Donuts

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Wildberry was a solid win to start our trip, and now we had to close in style. On the way to the airport, we came across this little donut shop that advertised “Chicken and Donuts.” I couldn’t believe my eyes, and my stomach could not fathom this concoction since I’ve never experienced anything of the like. We had no option but to give Do-Rite a try.

Let me tell you, we were not disappointed! Josh started with the Breakfast Sandwich with bacon, while I opted for the breakfast sandwich with bacon between a glazed donut. Then we each had a donut of our choice; you cannot go wrong here.

By Josh’s account, “this is the best chicken sandwich I’ve had in my life.” He still stands by that statement today. However, he suffers deeply from FOMO and he knew I had out-ordered him. This required seconds and he later returned with a breakfast sandwich between a glazed donut. I doubled down and elected for another myself. These were later cherished on the plane ride home.

Lou Malnati’s Deep Dish Pizza

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Ask anyone in Chicago where to get deep-dish, and you’ll receive answers from small, mom and pop shops, to the bigger name guys with a plethora of locations, but one name kept coming up: Lou Malnati’s.

Be prepared to wait or attempt to steal a seat at the full-service bar. The wait at dinner averages well over an hour. We were some of the lucky few to snag a bar stool and started with a cold, local brewski and fried calamari. You’ll want to start with an appetizer because the food itself takes close to 45 minutes, due to limited oven space and a vast amount of orders.

Order of choice: The Malnati Chicago Classic. “Made with Lou’s lean sausage, some extra cheese and vine-ripened tomato sauce on Buttercrust.™ It’s authentic Chicago!” This “lean sausage” was like any other I have encountered. It covered the entirety of the pizza like a sausage patty laid across the top of the pizza. Combined with melting cheese, an unbelievable tasty crust, with a little side of ranch dressing made for a beautiful sight and again, another successful meal in Chicago.


If you’ve read up until this point, you may be under the impression we hopped from one spot of gluttony to the next. Let me assure you, these meals were very spaced out, and we walked over 35 miles during our stay, most of that covered in gear, luggage, and expo supplies. We were working for these indulgences!

Swimming in Lake Michigan


We arrived in Chicago in early May, this meant the weather was beautiful, and the temperature never reached above 75. However, the water temperature was still an abysmal 42 degrees.

Our previous open water swim was conducted in Texas in the comfort of 70-degree water and 90 plus degree weather. This was going to be a little shock to the system, but it was time to test out the cold exposure training we had been practicing. To find out how we prepared, read on here.

As we dressed in our wetsuits, we got some crazy looks, a few shakes of the head, and a lot of pointing fingers. I could just imagine them all saying, “look at these knuckleheads, they’re probably foreign or from someplace like Texas. Idiots…

To which I would reply, “I’ll be your huckleberry!

After we had hit the 400m buoy, we decided it best to turn back and assess how we were feeling. Remember we did not have socks, gloves, or headgear so the extremities were exposed and you lose the majority of your body heat through your head. We wanted to play it safe.

It turns out this was a good call. On the way back to shore, my lats and shoulders began moving in slow motion and my feet felt tingly. We decided 15 minutes and a half mile was a long enough swim for the day, although if we had the time we could have taken a short break and gone for round two; freaking conferences…

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To give you a better idea, we swam at Ohio Street Beach, which came recommended to us by a colleague who also does Ironman Triathlons. The beach is calm which makes entry painless and the buoys are measured exactly 400m from the shoreline.

If you trek further down Riverside Drive, the beach begins to look like an actual beach with breaking waves and an undertow. A calm beach made our cold swim a little more manageable and pleasant. Not to mention the water was some of the cleanest, clearest, and most beautiful water in which we’ve had the opportunity to swim. Gorgeous!

I would recommend waiting for warmer weather, a wetsuit, and at least 6 weeks of our cold exposure protocol before you attempt the same. And always swim with a buddy when possible.

Running through the city/river walk

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We were surprised to learn that despite the relatively cold weather in Chicago, it’s an incredibly active city. It’s a common occurrence to see running groups, cyclists, dog walkers, and yogis on the river walk at any time of day.

For round one, Josh and I opted for a morning run along the river walk, but somehow we wound up amongst the hustle and bustle of the city. We soon found ourselves waiting at stoplights, dodging cabs, and trying aimlessly to circumvent the morning foot traffic. Let’s just say it slowed our mile time down a tad.

Lessons learned: the Riverwalk through the city is not continuous. You will be forced off at points, and cars do not habitually yield to pedestrians (even if you have the right of way). Also, Chicago sidewalks are not the most runner-friendly during the mass commute hours, and the inner city is MUCH more hilly than one would assume.

Next time we mapped out a route to stay along the shoreline and had a much more enjoyable experience.

Wrigley Field


There are a few hopes of every real baseball fan: to see the Yankees play in the original Yankee Stadium, watch the Red Sox play amidst the Green Monster’s backdrop, and catch a day game at the legendary Wrigley Field. Sadly, one of these will forever be only a dream.

After we had finished with our event, we caught the first cab we could and quickly made haste toward Wrigley. I always knew it was tucked away in a neighborhood and would be a smaller stadium due to its age. What I did not realize was how enveloped into this neighborhood the field actually is, and how small the stadium compares to its competitors today.

We’re used to seeing colossal stadiums built as a major footprint in a city. They are built with the highest technology available, on the largest lots available, to seat as many people as possible, and ultimately become a major disruptor in the city on game day. And nothing is inherently bad about any of this.

However, Wrigley was like finding a hidden jewel, her vintage red brick revealing her age, surrounded by eclectic, craftsmen homes resembling the turn of the century.

We made our way to the ticket gates, and we arrived right on time. Not the start of the first, but the start of the seventh.

*Little known fact: Some major league franchises still honor the age-old of free entry after the start of the seventh inning. Free baseball!

It was a cold, crisp evening and we found seats along the third baseline. After an inning, we decided we deserved even better seats for this once-in-a-lifetime experience. We walked around toward home plate and filed into a couple empty seats just five rows up.

My first and only thought: THIS. IS. AMAZING!

Luckily we witnessed the Cubs win as well as the “Go Cubs Go…Go Cubs Go…Hey, Chicago What do you say, the Cubs are going to win today,” melody after the game. The place was rocking!

The party moved just up the street to the bars that lined the streets of Wrigley, dubbed Wrigleyville.

We soaked in the atmosphere as long as we could, grabbed a couple cold ones in Wrigleyville, and celebrated like we were lifelong Cubs fans. This was a day I will not soon forget.

Navy Pier

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I was not going to mention Navy Pier, but if you Google “things to do in Chicago,” this will inevitably result, so I’ll mention it.

Navy Pier played host to the expo we were attending, and although we did not participate in any activities on the pier, a few walks around the place and you get the gist. They have a Ferris wheel (non-operational at the time), food and restaurants, boat tours of the lake (they will solicit you), a Children’s Museum, and plenty of gorgeous views.

We decided not to spend much time there because; like I said you get the feel of the place after one walk through. While it’s beautiful and worth seeing if you have the time, I wouldn’t spend any money there unless you have children that can enjoy the museum, Ferris wheel, and food stands.

With all that being said, thank you Chicago for hosting The Too Fit Guys. We will undoubtedly be back! If you agree we did right by Chicago, or if there’s anything we missed, please let us know in the comments below.

P.S. I nearly forgot to mention Josh’s favorite part of the trip: the tulips. Yes, tulips. The whole town was covered in them during our stay and truly brought out his childlike wonder. Every corner we turned was quickly followed by, “Wow, I cannot get over these tulips! I’ve never seen anything like this. They’re gorgeous!” Therefore, if there is ever an occasion for you to bring Josh flowers, tulips will surely do the trick.