Chicago River

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Chicago flag

First, let’s clear something up that we learned on our recent visit to Chicago. The Second City got its moniker not from playing runner up to New York, but rather during the historic rebuilding of the city after the devastating fire of 1871. Make no mistake, this is a world-class city that stands out on its own. Chicago boasts one of the cleanest downtowns of any American metropolis, along with a wide variety of cultural institutions and a booming culinary (and beer) scene. The architecture is magnificent and the people are friendly. But they’ve all got opinions on which neighborhood is the best.

Speaking of which, Chicago is home to 77 individual neighborhoods, so don’t think you’ll be able to cover them all in one visit. There’s a lot to do and plenty of ways to get lost and make your own serendipitous discoveries. But to help you navigate, we’ve put together an ideal itinerary for a quick weekend trip with the best places to stay, drink and discover.

Words by

Cory Ohlendorf

Photography by


The Vitals

The best time to go ...

Summer and fall are ideal times, as the weather is agreeable and there are plenty of street festivals, exhibitions and sporting events. This is also when the lakefront is buzzing with activity. Winter, as you've likely heard, is no joke here.

The 'L' train in Chicago

Getting around ...

The network of subways and elevated trains (all of which is referred to as “the L”) services the city's vast network of neighborhoods and even some of the larger suburbs. At $2.50 per ride, you may want to consider a single day or 3-day pass.

Did you know? ...

Chicago has the most breweries in the United States, according to Brewers Association.

A town of many nicknames ...

The Windy City, The Second City, City of Big Shoulders and The City That Works.




We touchdown on a sunny afternoon in Chicago and hop on the train towards downtown. The Hoxton is located in the heart of the now-bustling Fulton Market District. Once an industrial area, it's transformed into a hub for stylish, creative types—brimming with shops, galleries and some of the city's most buzzed about bars and restaurants. The lobby is a proper living room environment, with lots of people tucked into corners and lounging on velvet sofas in front of the massive fireplace. (Later, we'll head downstairs to the Lazy Bird speakeasy where they make a mean Negroni to the sounds of live jazz.)

The Hoxton hotel in the Fulton Market District of Chicago, Illinois

The Hoxton hotel
in the Fulton Market District

The Hoxton hotel
in the Fulton
Market District

Upstairs, we find our room to be both plush and practical. The rooms aren't huge, but they're expertly and efficiently arranged. There's a king bed with a leather headboard and reading lights, a lounge chair with ottoman and a very sexy bathroom outfitted with Waterworks fixtures and a shower built for two. The floor-to-ceiling views let us marvel at the glistening silver streak of the L train rushing by without ever actually having to hear it. The details of the room are what's to be appreciated though. Midcentury meets Wes Anderson, everything is sharp yet charming. There's a bedside bluetooth Marshall speaker along with a selection of curated books and the coffee mugs and glasses are luxe.

What's more, there's also a handsome coworking space located in the hotel—perfect for those of us who can't quite get away, even on vacation. We grabbed a Day Pass and headed up to the space where comfy chairs, plenty of outlets and complimentary coffee ensures you get everything you need done. Finished with work and fully caffeinated, we're ready for a little exercise. And on a beautiful day, you'd be hard pressed to find a better activity than biking along the lakefront trail hugging the shore of Lake Michigan.

Cut through Millennium Park, a 25-acre park filled with public art, and stop to take the requisite selfie in front of Anish Kapoor's mirrored bean-shaped sculpture "Cloud Gate" that does have a miraculous way of drawing the eye's attention. Just past the sweeping stainless steel bandshell (designed by Frank Gehry), there's a winding, serpentine walkway over busy Columbus Drive that leads to the lake. Divvy bikes, which are prevalent throughout the city, are right there and make it easy to hop on and start riding.

Millennium Park in Chicago

Millennium Park

Millennium Park

Divvy rental bikes in Chicago

There are more than 18 miles of well-paved trails to take on, so the question is which way would you care to go? We suggest you bike north along the lakefront up to the charming, retro neighborhood of Andersonville. Here, you could do a little shopping—specialty stores abound, from books and music to a very cool vintage shop, Brown Elephant Resale Shop, housed inside the historic 1915 Calo Theatre. Then, relax with a cup of coffee and something sweet at First Slice Pie Shop. Afterwards, hop back on the bike trail and pedal back south, eventually winding past the famed Buckingham Fountain and ending your ride at the Field Museum, a neoclassical shrine to the natural world where you can cool off and take in such exhibits as towering dinosaur skeletons and a three-story ancient Egyptian tomb.

Giant restaurant in the Logan Square neighborhood of Chicago

Giant in Logan Square

Giant in Logan Square
and drinks at Cindy's in The Loop

After all that biking (and ideally a shower), you'll be ready for dinner. We've heard nothing but good things about Giant and decide to test our luck and show up early without reservations. With only 45 seats available, tables at the stylish award-winning spot in Logan Square are hard to come by, but the relaxed back patio is available for walk-ins. We get seated at the chef's bar by the kitchen, which is like dinner and show, watching the talented kitchen staff compile each thoughtfully prepared dish. After sharing plates of saffron-scented tagliatelle with Dungeness crab and harissa lamb with artichokes and dates, we decide we can't eat anymore. But we could maybe drink.

End your night at Cindy's, the rooftop bar at the Chicago Athletic Association, for a nightcap with a spectacular view. The open-air terrace specializes in artisan cocktails and the old school environment makes for a relaxed way to wind down at the end of a long day.




Stan's Donuts shop in Chicago

Grab a quick breakfast of freshly made donuts (we suggest the Biscoff and apple fritter) at Stan's Donuts, just across the street from the hotel. Nurse the rest of your coffee as you meander up Michigan Avenue while taking in the iconic architecture, from the stately Wrigley Building along the Chicago River to the John Hancock Tower. The well-manicured sidewalks along the Magnificent Mile are home to some of the city's best window shopping. Now is also a great time to pop into a museum before the crowds come and the Museum of Contemporary Art's ever-changing exhibits definitely make it worth a visit. Through the end of September, check out Virgil Abloh's "Figures of Speech" exhibit.

A truly unique way to take in the city is to book an architectural tour on the Chicago River, which cuts right through the middle of town, requiring more than 40 drawbridges to stitch it back together. The Chicago Architecture Foundation river cruise is a relaxing and entertaining boat tour that supplies some of the greatest views of the city's most legendary buildings. And since you're right on the river, why not explore the newly revived river walk? Spanning over six blocks, it offers uninterrupted pedestrian paths plus restaurants, live performance seating and grassy areas to sit and people watch.

Off Color Brewing in the Lincoln Park neighborhood of Chicago

Off Color Brewing in Lincoln Park

Fully relaxed after a boat ride, there was nothing left to do but day drink. Thankfully, the Chicago locals we were with knew just where to take us for a cold craft beer. You see, there are no shortages of breweries in Chicago and Off Color Brewing was just a few stops away on the L. The taproom and beer garden serves up a wide range of microbrews and innovative beer cocktails, while local restaurants prepare small bites. Of course, that wasn't the only brewery our drinking buddies brought us to. We also hit up Revolution and Hopewell while in town.

Salvage One in Chicago

Salvage One in West Town

Buzzed and ready to do a little shopping, we hop in a Lyft and head to Salvage One. The sprawling 60,000 square foot warehouse packs in truly unique vintage finds, antique furniture and architectural salvage items such as columns, old signs and even a hand-carved oak bar saved from a tavern before demolition. Just down the street is Stock Mfg. Co., a handsome store and workshop that offers workwear and menswear in a ruggedly masculine environment.

Eventually, we make our way back downtown where there are some serious contenders vying for your dinner dollars. Such buzzy, award-winning eateries as The Publican, Au Cheval and Duck Duck Goat are all in about a three-block radius from one another, so if you can't get into one, try another.

ComedySportz improv comedy in Chicago

ComedySportz in Wrigleyville

End your night with a little improv. Chicago is famous for its comedy and has plenty of improvised comedy shows to choose from with more than 70 listings on Yelp. The most famous, of course, is The Second City but one of the funniest is ComedySportz, an interactive show where two teams create comedy scenes, songs and games right on the spot based on your suggestions.




When asked where we should head for breakfast, more than one local advised us to try Goddess and the Baker. Located in the shadow of the L tracks in the city's South Loop, this place will satisfy anyone with an appetite thanks to a mix of generously sized baked goods and healthy, clean options.

Bonci pizzeria in the Bucktown neighborhood of Chicago

Goddess and the Baker in The Loop, Bonci pizzeria in Bucktown and Topdrawer in Wicker Park

Goddess and the Baker in The Loop,
Bonci pizzeria in Bucktown
and Topdrawer in Wicker Park

Next, head north to Bucktown and Wicker Park, sister neighborhoods of sorts. Just steps from the Damen L station is Bonci pizzeria. This Roman-style pizza joint serves up handcrafted pies that you can buy by the inch. It's an ingenious way to sample a variety of seasonal toppings, of which they have plenty. We tried the soppressatta, Parmigiano with fried onions, ricotta with zucchini and lemon zest, along with a surprisingly delicious blueberry and sausage.

Shinola cola

The neighborhood is home to a wide range of great shops and galleries. There are small, unique spots like Topdrawer (full of cool Japanese tools and gear) as well as a few of our favorite shops, from Aesop to Shinola, where a friendly associate delighted us with an icy bottle of their house-branded cola.

The 606 Bloomingdale Trail in Chicago

The 606 (aka Bloomingdale Trail)
in Bucktown and Wicker Park

While in the area, don't miss out on the 606 (also known as the Bloomingdale Trail). The former elevated train tracks have been turned into a three-mile long walking and biking path that connects four popular neighborhoods. Planted with local wildlife and a number of art installations, the lofted park is a pedestrian-friendly east-west thoroughfare that offers a green escape from the busy streets down below. And with 12 different access points along with 17 ramps for those with disabilities, the well-kept trail is easy to access too.

Fat Rice restaurant in the Logan Square neighborhood of Chicago

Fat Rice in Logan Square

For dinner, you're not too far from Fat Rice in Logan Square. Here, flavors from China, India, Southeast Asia and Portugal fuze in a menu meant for groups to share. Make sure to order their signature "Arroz Gordo," an overflowing clay pot of spiced jasmine rice, chili prawns, curried chicken thighs and char siu pork, topped with a tea-brined egg.

Lost Lake tiki bar in Logan Square neighborhood of Chicago

Lost Lake tiki bar
in Logan Square

Lost Lake tiki bar in Logan Square

After dinner, head to Lost Lake, a tiki bar that's hiding behind an unassuming plain brick facade. Inside, however, is a veritable fever dream of tropical delights and midcentury glamour. The atmosphere is relaxed and warm and the drinks are delicious, inventive and flamboyantly garnished. From a classic Hemingway daiquiri to a more outrageous "Salty in all the Right Places" (with Overproof Jamaican Rum, coconut and absinthe), there's something to suit any drinker's proclivities.

I wouldn’t say that Chicago is known for its indulgences, but the hearty Midwestern fare mixed with the city’s relaxed attitude and welcoming hospitality somehow lends itself to just letting go and having a good time. After all, life is short. Spend a lazy afternoon on the river or get lost in a museum. Have a picnic by the lake. Order another beer, maybe one more slice of pizza or grab a bag of mid-afternoon caramel corn from Garrett’s. No one is going to judge you ... those midwesterners are too pleasant for that.

Further Reading

Not For Tourist Guide to Chicago

$12.51 at Amazon

Not For Tourist Guide to Chicago

$12.51 at Amazon

The Not For Tourist Guide to Chicago is a handy, map-based handbook that divides the city into 60 mapped regions to break down the various neighborhoods. And every map is dotted with user-friendly NFT icons that plot the nearest essential services and locations.

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