Greetings fellow nomads! As promised, we’re back with our latest journal entry after a fun, fall weekend trip to Chicago. This excursion was an interesting one since I accompanied my first client on the journey as my girlfriend wanted to take me somewhere for my birthday. Full disclosure, yes I know this is shameless self-promotion, but it did also give me the opportunity to see firsthand the offerings that our partners at Fora Travel can provide for our clients. Huzzah!
Day 1: Travel Day and Hyde Park with Friends
Our trip to the Windy City started with a car journey from my home in Kalamazoo to…Michigan City, Indiana??? You may be asking yourselves why we’re driving to Indiana, and trust me there’s a great #travelhack of a reason. From most cities in the Midwest, your options to get to Chicago are either driving or taking Amtrak trains. Driving sounds great in theory, but then you get to the city and you’re faced with anywhere between $25 to $100 daily for parking fees. In Amtrak, my love-hate relationship with our national passenger carrier continues. Amtrak can be an affordable alternative, particularly in states where trains are state DOT-subsidized (i.e. Michigan, Illinois and Wisconsin), but trains are not as frequent and cost can be $50-100 round-trip.
Commuter rail has entered the chat…
The reason for going to Michigan City was to take the South Shore Line to Downtown Chicago, which is a commuter line that costs $11.50 one-way and has multiple departures per day to maintain flexibility. The ride through Northern Indiana was straightforward and more importantly, parking at the train station is free so this hack has the potential to save you hundreds of dollars over a weekend or week in Chicago (Metra rail is the Chicago-area commuter service in Illinois–also highly recommended).
Once we arrived at Millennium Park Station, my companion and I took a very breezy and festive walk up Michigan Avenue, over the river and through the woods[?], to River North to our hotel for the weekend, The Gwen. The property is a very charming, artsy hotel that is part of The Luxury Collection brand by Marriott. Yes, the word “luxury” is in the name, but The Gwen (521 N Rush St, book via Marriott.com) has a mid-market price point for Downtown Chicago hotels (~$250/night) and was a great find in terms of value and location. Booking with Fora, my client was able to receive a $100 food and beverage credit, free breakfast, and a delightful welcome package in the room containing a bottle of French red wine, cheeses and macarons…Mais oui! The staff were incredibly pleasant, the restaurant and bar menus were novel and curated by professionals. The views were exquisite and observing my Michigan State grad of a partner around an influx of Maize and Blue with a Michigan football game that weekend was quite amusing.
The remainder of our first day was spent with a college friend of mine and her family. She lives in Hyde Park on the near south side of the city. The neighborhood, against the backdrop of the University of Chicago, is very pleasant to explore with a mix of historic and modern homes. It did harken back to a time during the Obama Administration where I was chased down by the Secret Service hauling wedding gifts in a restricted area, but I digress. Consistent with the theme of accessibility by transport, we were easily able to get to her house without a car using Metra rail and our walking legs–much of the city is like this (another reason to abandon the car at a parking lot in another state). Without going into too much detail, the foodie portion of our journey started off with pizza from Pizza Capri, a small local chain that specializes in both Chicago Deep-Dish and Thin Crust–locals do indeed eat both, despite urban legend that Deep-Dish is only for tourists. Our hosts were vegetarian and Capri did not disappoint, with a very well-seasoned spinach Deep-Dish, and delightful Cheese and Veggie Supreme offerings, respectively. I had never heard of this particular restaurant before, but I’ll definitely call it out as a great local find if you’re in the area.
Day 2–Fulton Market, Urban Foraging (part 1):
Anyone familiar with mysteries, true crime podcasts, or dating knows that returning to the scene of the crime is less than ideal when things go sideways. A couple weeks before our Chicago trip, I was in the city for what I know now was a job interview with a sub-optimal outcome in the Fulton Market neighborhood of Chicago’s West Loop.
In spite of the short-term setback, I saw something different in this area after years of being told the West Side of Chicago was less than safe and set out to explore with my girlfriend on our second day venturing out. I’ll give all appropriate warnings about gentrification, which has its social concerns, but can also represent investment that did not previously exist. On initial appearance, Fulton Market is an interesting mix of modern buildings and retrofitted architecture leveraging buildings from the area’s industrial past…the industrial past did not have food like this.
Our reasonably mid-market foodie odyssey started at a location where we were greeted by a painted tiger with a top hat on the building and signs extolling the establishment as a purveyor of sausage, bacon and beer. To this effect, Kaiser Tiger (1415 W. Randolph St) did not disappoint. The environment was that of a neighborhood tavern but I would hesitate to call it a dive bar, more like a dive bar’s professional cousin who’s a little put together but still sports a clip-on tie. It was a warm environment with a solid regional craft brew game, fun group activities like games on a shelf and even a vending machine with mini-crafts to work on, and apparently curling leagues in the winter? And then there’s the meat. My girlfriend and I ordered the Bacon Board and it did not disappoint…FOUR different varieties of bacon including Canadian, plain Jane, peppered and candied with a very tasty stone-ground mustard and crostini to match. It doesn’t sound like much, but you’re curating meat with a great presentation. What’s not to like?…more pretty curated meats later. Also notable was the Bavarian pretzel the couple next to us ordered that was the size of a small child. I did not walk over and ask for a sample, but I can recognize a distinct lack of talking and happy mouths eating anywhere. Everyone’s experience is going to be a little different, but I would recommend Kaiser Tiger as a stop.
Continuing to wander up Randolph Street, I can say that Fulton Market is very walkable and, like most of Chicago, readily accessible by public transportation by the CTA Green Line–Morgan Station. I found that shops, bars and restaurants were primarily along Randolph St. and Fulton Ave, but I would not neglect the side streets in the area since there are a number of other small businesses worth your attention. Our next stop was NOT a small business…but none other than McDonald’s vaunted and somewhat mythical Hamburger University (yes, it exists…at 1045 W. Randolph). The building itself is McDonald’s training facility for its employees. I am less interested in that and more in the nondescript McDonald’s restaurant on the ground floor. This is not your McDonald’s around the corner, but more a living urban legend. At this site is the McDonald’s with a secret menu, not advertised to outsiders and only provided once you walk in, which showcases both international favorites not available in the United States, and test menu items that may never see the light of day. According to some intel we received, the menu rotates every three months and is being updated for the Christmas season…in short, stop by for tasty treats! The menu item we tried was the Biscoff Caramel McFlurry from Belgium. I cannot say enough about this dessert…it is everything you want in a soft-serve but the pairing of Biscoff cookie bits with caramel was so rich and delectable that you have to taste it to believe it. Sure, you could try to replicate it, but this dish is best left to the professionals.
Our last visit in Fulton Market was another dessert stop, because we were walking around a lot and I’m a grown man, don’t judge me! I will walk into Jeni’s Splendid Ice Creams (908 W. Randolph St) and try all the things. You may recognize Jeni’s since their ice cream is available commercially, at least I’ve seen it regionally in the Midwest at my grocery store. The flavor range is such that the sample spoons are plentiful and the kind woman behind the counter seemed more a museum docent of ice cream than just someone scooping dessert. Flavors ranged from Cranberry Panettone with Chocolate Sprinkles to Boozy Egg Nog to Cold Brew with Coconut Cream. Strongly urge you to try a few, even if you don’t want the whole bowl or cone. My personal favorite was Buttercream Birthday Cake, which well…it was a birthday trip so I felt some obligation. The ice cream was very rich, decadent and delightful…and I didn’t have to bake a cake in a strange place, which is also a plus. The location was spacious, with fun decor and good company. Not a bad place to hang for a minute on a wildly-unseasonably-warm November day at 60+ degrees!
Moooo-ving right along, we left our street food odyssey and returned downtown for dinner later in the day. Jose Andres is my favorite celebrity chef for a variety of reasons–namely his caring yet funny personality, worldwide charity work for disaster relief and aiding those having difficulty accessing food. To go to one of his restaurants for the first time was literally like being a kid in a candy store…a candy store with racks upon racks of dry-aged meat at Bazaar Meat (120 N Wacker Dr). I cannot say enough good things about the place–the experience was definitive fine dining with front-of-house staff that were kind yet meticulous in getting every detail right–for instance, the sommelier was visibly frustrated at the lighting in the dining room being changed so we couldn’t see the color hue of our rose. I had one of the best steaks I’ve ever eaten, and accompanied by a very worthy supporting cast. I’ve never seen a caprese salad made with molecular gastronomy technique, and the Caipirinha cocktail I ordered was made tableside with liquid nitrogen–all I can say is the science nerd in me was dancing. The grilled octopus, flavorful sauces like mojo picon and bechamel for the croquetas, and quality ingredients like paprika and olives brought a Spanish flair that I enjoyed immensely. The one aspect I did not expect was how approachable Bazaar was. I was slightly dressed up (suit, no tie), but I would describe the vibe as business casual and the price points, even for a tasting menu at $145, were solid for visitors like myself wanting high quality food but not necessarily the most expensive bill. After saying farewell to Bazaar, we were treated to artisan cocktails on the rooftop patio at The Gwen…yes, there were spectacular views from the River North hotel location and, more importantly, there’s plentiful outdoor heaters! Don’t let playful drink names like The Magician, and NA-Groni (Dad Joke Special, that one) and The Fool…fool you. Definite care was taken in making these libations. This visit proved to be a relaxing end to our evening, with a ruff start planned for tomorrow.
Day 3–Urban Foraging (part 2), Music and Puppies???:
No, that was not a typo above…our last day in Chicago started with yoga, but not just any yoga…yoga with puppies!!!. My girlfriend and I had visited Puppy Sphere on a trip earlier in the year to California and loved quality time with their downward dogs, so that motivated us to visit their West Town location without hesitating (1105 W Chicago Ave). The team at Puppy Sphere was incredibly friendly, the instructor put together a great workout and the white French Bulldog puppies were covered in gray spots and loved all the attention. Even looking at the side rooms and seeing the facility where the doggos were kept, it was clear these very much available for adoption pups are well-loved and cared for. One in particular stuck to me like glue to the point where I just needed to stop and cuddle…look at it this way, either you find physical or mental well-being in this spot so you have no reason not to visit, aside from maybe allergies or if you’re a cat.
The penultimate stop on our voyage was the Chicago Loop Food Walk, curated by our partners at GetYourGuide. The premise was simple: We wander the downtown area, grab some iconic eats and get all the cliches from a generic tour guide, right? Not quite. Our guide, Dash, met us under the marquee of the Chicago Theater and started us on our hike of the urban jungle. He told us where we were going, and I felt like we were following the usual script since Portillo’s and Lou Malnati’s were on the list, two recognizable chains that got their start locally specializing in Italian beef and pizza, respectively. That was where the conventional ended, to the tour’s credit. My companion and I were joined by another couple on the tour, but interestingly enough, they were from the city! It turns out that Dash is very well-versed in the city’s history, to the extent that he could point out a couple of the structures still standing from the Great Chicago Fire (you can still see the black smoke marks on the roof!), told of tales from the mobster days and the rivalry of Dean O’Banion’s Irish mob faction, and a little known underworld figure named Al Capone. We also were taught how many parts of downtown were literally jacked up to get the city out of the mud. Dash even took us on an unofficial excursion at the end through Merchandise Mart, which honestly is one of the strangest buildings I’ve ever been in. It is a giant showroom for all things luxury…want a $10,000 stove and range for your home? It’s there. Apparently world royalty send personal shoppers there to deck out their palaces even. While this is very abstract for a food tour, I appreciated the care that was taken to show us around. And then there was the food…nom nom nom. Lou Malnati’s is my favorite Chicago deep-dish so that wasn’t exactly difficult to swallow. However, Portillo’s admittedly isn’t my favorite and I have a vendetta against raw tomato on anything so a Chicago dog proved very daunting for my pallet. I persevered and could bear the Italian beef (see what I did there?) and the dog served up by a nondescript neighborhood joint called Mr. J’s was nothing short of sweet and spicy goodness. Local food favorites served up with a few historical amuses bouches hit the mark on this tour.
Our final location paid homage to the music tradition of Chicago. We went to see some local pop-punk purveyors of my youth at the House of Blues (329 N Dearborn St), Lucky Boys Confusion. Live music in Chicago is an experience, given the legends who piled their trade there over the years. From the bluesmen that made their way to Maxwell Street in the Great Migration and later contemporaries like John Lee Hooker and Buddy Guy, to rocking modern native sons like Wilco, Rise Against, and Smashing Pumpkins and more, expect even a show with local talent to be a quality experience. Yes, I know that the HOB is somewhat corporate, but I still think they make a good faith attempt to keep an artists’ atmosphere alive with no shortage of work from creatives adorning the walls and it felt warm and welcoming on my second visit to the venue. Lucky Boys Confusion were great, as I heard familiar tunes Fred Astaire and Hey Driver, but also tracks from their new album Soapbox Spectacle that were solid. Perhaps more striking to me was one of the new-to-me opening bands, Guardrail, which had a playful but edgy punk sound that left me looking for more (you won’t be disappointed); and that it was an all-ages show. When I think all ages, maybe there’s a few 15 year-olds who get their hand stamped so they don’t drink…not here, friends. They “turn it up to eleven” with whole families, some featuring 3-4-5 year olds in airport ground crew headphones. I’ve never felt like a less cool parent in that environment. Despite nursing my bruised cool dad ego, I enjoyed myself and didn’t feel too claustrophobic in General Admission. My best advice is wear comfortable shoes if you’re on the floor, but that’s true of concerts everywhere…and go for the premium beer over Miller Lite or Bud, it’s like $1 more.
Looking back on our Chicago adventure, our merry traveling party held true to avoiding touristy experiences to the extent possible and seeking out a true local experience. Fortunately, for Second City dwellers and visitors alike, there is no such thing as Point A to B and always taking the same path. Chicago is “Choose Your Own Adventure” on performance-enhancers. Every block, every wrong turn, every individualized experience can change the story. I guess the moral of the story would be to be brave and challenge any assumptions you may have had. As a famous, yet fictitious, local once said “If you don’t stop to look around once and a while, you could miss it.”
Key Takeaways / Hacks:
- Use commuter rail and public transportation where possible, even if you’re flying into the city. It will save you a significant amount of money on parking in the Downtown Chicago area.
- For accommodations, high price point often does not equate to high value. Fora-affiliated travel advisors, like Those Who Wander, can access perks and upgrades not available to the general public and we can help you with finding a premium experience for a mid-market price.
- Step out of the normal “touristy” experiences once and a while. You may be surprised by what you find.
- Don’t be afraid to eat the good stuff in Chicago. You’ll do plenty of walking anyway.
- Go do puppy yoga, play with all the doggos.
- Punk rock toddlers will always be cooler than you. I don’t make the rules.