Chicago in 72 Hours

By Josh Baldwin

Chicago is full of can’t-miss foodie destinations and three days ain’t gonna scratch the surface...but we did our best. The new flights from Lewisburg land at O’Hare in time for dinner and a night on the town, so grab an Uber, check into your hotel, and head back out to make the most of your late afternoon arrival. Wear your walking shoes and make sure your belt has an extra notch.

Day 1

After a quick check-in at the Kimpton Monaco, with fantastic views over the Chicago River and easy access to all the points in town, we headed to the ever-evolving West Loop area for dinner. The West Loop is a former warehouse and factory district just on the edge of downtown. Its spaces are quickly turning into some of the hippest hot spots in town and the food scene is a driving force in that movement.

We stop for a quick drink at the funky latin Bar Takito, where the cherry-infused, smoky mezcal cocktail named Mouthful of Diamonds glows ruby red, and the more classic “My Lemonade Romance” (vodka, tamarind, lemonade), make for a great start to the evening.

Around the corner and down a couple blocks, we take in a few appetizers at The Publican. One of Eater’s top restaurants in the country, The Publican offers communal seating as well as private booths. They pride themselves on beer, oysters, and pork, three of our favorite food groups. Needing to take it easier, since we had late-night tasting menu reservations, we dove into a plate of oysters—two of each variety in the house, including Lady Slippers (Prince Edward Island), Wildcat Cove (Puget Sound), and Aunt Dotties (Massachusetts). Our flights of beer had a healthy mix of sour sessions and light ales.

A short stroll down Randolph Street and we find ourselves at Smyth, John and Karen Shields’ triumphant return to Chicago. (We featured the Shield’s restaurant Town House, in Chilhowie, Virginia, in issue 39).  

“Town House was our first restaurant where we were able to completely craft our own vision for the concept,” says Karen. 

Dessert at Smyth, an egg yolk soaked in salted licorice with frozen yogurt meringue (photo by Huge Galdones

@galdophoto.com).

“It was amazing,” adds John, “but we decided we wanted to return to Chicago to raise our family and build our dream restaurant. Thus, Smyth + The Loyalist was born.”

Our meal at Smyth started off with a bottle of Champagne and an oyster and seaweed “shot” with salted raspberries and radishes. The 5-course tasting menu (they go up to 19 courses!), known as the “Classic” menu, was highlighted by 128-day aged ribeye with sprouted wheat and sorrel, served with aged jus and a brioche bun. The dessert plates were punctuated by a beautiful dish of milk chocolate with raspberries, berry sauce, shiitake, and kelp. Smyth was awarded two Michelin stars last year, but the dress code and attitude are “come as you are.” If you’re looking for one of the best tasting menus in town, don’t miss this gem.

Lamb Breast with Soured Cream and Trigo Fuerte

Milk Chocolate, Raspberry Preserves, Shittake, Kelp

Other West Loop faves: The Aviary, Grant Achatz’s avant-garde cocktail bar (reservations required); Top Chef’s Stephanie Izard’s flagship restaurant Girl and the Goat, as well as the Little Goat Diner across the street; Lou Malnati’s Pizzeria is a must for those looking for some of Chicago’s best; Au Cheval has one of the city’s great burgers and beer menus.

Day 2

Today we headed to Logan Square to the Bang Bang Pie Shop for some breakfast. Homemade biscuits are what you are having for breakfast, and they come in a variety of combinations. Outdoor seating is plentiful and the vibe is very progressive and hip. Down the street you can shop the Logan Square district’s boutiques. 

For a quick lunch we decided to eat light (big dinner coming up tonight!) so we went to Grant Park and hung out and ate at some street vendors for snacks. Sorry, no Chicago hot dogs or Al’s Italian Beef on this day!

Now for this evening, we had a special dinner, not for the faint of heart. Alinea is consistently on the World’s Best list, and its chef has also graced these pages before as a coach of the Bocuse d’Or team of Rich Rosendale and Corey Segiel, as well as appearing in my documentary “The Contender” about that experience. The reservation system is actually a ticket for dinner. You buy the table (the entire table, for the evening), add your level of wine pairing, and pay all tipping and taxes before you ever arrive. You can even add gift items. We bought a table for four for the Salon Seating, which is upstairs and about four to six courses less than the Gallery Seating, which is located downstairs on the main room. Don’t stress over which seating you get. Just get the table if it’s available and close your eyes when you pay.

Mary and I wound up taking my great friend Becky Ward from high school and her husband Kyle Gibson. Both are Chicago-based actors, and while Becky had been to Alinea years ago, Kyle had not and, therefore, knew nothing of what he was getting into. The experience at Alinea can be the height of pretension for some. And there’s a valid argument for that...in some cases. But I think that can be very reductive and expresses too narrow-minded a view on what food can be. Yes, there is room for both a Mickey with extra cheese from Tudor’s and snap peas that float on an Irish linen pillow full of lavender air (one of Achatz’s more famous dishes, featured on his episode of “Chef’s Table”).

Dinner, if you could call it that, started with an iceberg “terrarium” atop a shard of steel mesh—a steampunk sculpture juxtaposed against a small wooden bowl that, when opened, revealed smoked osetra caviar, with sunflower, onion, and lemon. After the dish was taken away, and just as I was mentioning how great the gigantic bowl of cut oranges in front of us smelled, two servers showed up to pour liquid nitrogen in the bowl, and for the next five minutes we enjoyed our next dish—spanner crab, coconut, curry glow and spiced orange—in a fog bank bright with citrus.

Iceberg Terrarium @ Alinea

Morrells, Ramp Sauce, Parmesan @ Alinea

As you might tell, dining at Alinea is not for everyone, but for those in search of once-in-a-lifetime experience, don’t pass up the chance at a reservation. Other highlights of the evening included seeing ramps on the menu during a dish called “Vibrant,” with morels, ramps, and parmesan, as well as “The Cape,” made of clams, potato, and bacon. Wine pairings were deep tracks from small vineyards, and the sommelier told stories about their provenance instead of esoteric tasting notes.

Having done the early seating at Alinea (there are two every night) we had plenty of time to explore the city. Our favorite rooftop bars were at the Robey Hotel and, conveniently around the corner from our hotel, the Cerise at the Virgin Hotel, with great views of the top of 33 East Wacker, also known as the Jeweler’s Building. Ground level, you can head over to Grant Park for an outdoor concert or late-night hot dog.

Day 3

We woke up to have breakfast at the hotel restaurant, which was starting to receive its own buzz. Fisk & Co is a Belgian-inspired bistro that terms itself a “Mussels and Beer Bar.” This morning, however, we were having neither. I opted for some Belgian Waffles and Mary opted for an omelet, before heading out to the Miracle Mile, just across the Chicago River from our hotel.

Just off Michigan Avenue, you’ll find one of Chicago’s most famous pizza spots—Giordano’s. Famous for its deep dish stuffed crust, Giordano’s is for the patient diner. Come at lunch and expect a long wait. If you can squeeze in a late-night dinner, this might be a good spot, too. Either way, you are waiting an hour for your pizza to bake. When it arrives, you will know why. The thing is as thick as the city’s phonebook, and must be washed down with a pitcher of beer.

We decided to book the famous Chicago River cruise this evening so we went back to Logan Square in the afternoon to hit up some cocktail bars for some well-deserved day drinking. The night before, Becky had told us not to miss Lost Lake Chicago, one of her favorite bars. That morning, as I was reading the morning news on my phone, I saw an article about the best bars in the world. The number one bar, in this Conde Nast article, is Lost Lake Chicago! Now I gotta go.

We got there just as they opened (back to Logan Square!) and saddled up to the tiki-inspired bar for a slew of tiki drinks with small-batch rums. Every drink in this highly creative bar is served in its own vessel and the surrounding decoration is Dorothy Draper meets kitschy Tiki Bar. Most drinks are for one person but some vessels serve up to four people.

Fun Drinks at Lost Lake Tiki Bar (photo by Clayton Hauck)

Just down the street, we fell in love with Billy Sunday. This is a cocktail lover’s dream, with a huge variety to choose from and tons of unique choices behind the bar. A guest bartender was rolling in when we were leaving and the place was filling up to catch a little of his magic.

We rolled back downtown to catch the sunset cruise with Chicago’s First Lady Cruises—another can’t-miss activity. There are many boat tours up and down the Chicago River, but this company seemed to be the best. Booked via Ticketmaster the day of, the cruise is narrated by Chicago Architecture Foundation volunteers and hits all of the highlights of architectural history up both tributaries of the river. Don’t fret when you see the long line, there is plenty of room on the boat. And if you can, take the tour as the sun sets, reflected in the tall buildings and casting glorious shadows across the city.

After leaving the cruise we walked back up to street level and found ourselves on Michigan Avenue. Exploring the Miracle Mile at night, it seemed to have a completely different vibe. We stumbled up Joe’s Seafood, Prime Steak, and Stone Crab—what could be mistaken for a Myrtle Beach All-You-Can-Eat-type joint, but instead makes a memorable impression. We opted for a little of each, ordering a seafood tower with stone crab, and a filet with bearnaise sauce. Everything was well executed, including the craft beer suggestions from our tuxedo-clad server. If you’re looking for some straightforward steaks and seafood, Joe’s is where you want to go.

The next morning we explored a little more, but for the most part we could absolutely not eat anymore. While we had hoped to hit a few more highly-rated spots—Gibson’s, The Violet Hour, Superdawg, Peqoud’s Pizza, Bavette’s, and the world’s first Michelin starred brewpub, Band of Bohemia—we still made a great play at mixing up long-held reservations with spontaneity. Two months later I feel like I’m still trying to figure out how to lose all the weight I gained.