What To Eat, Drink, & Just
About Everything Else
Near Our Boot Camp Chicago 2025 Venues
Chicago has MUCH more happening than we could possibly cover comprehensively, but we did want to arm you with a few categorized recommendations—some personal favorites, some from our Chicagoan friends—that are convenient to each of Boot Camp long-weekend's venues.
Choose a Boot Camp venue below to check out the guide!
BOOT CAMP MAIN EXPO VENUE
4325 N. Ravenswood Ave.
Note: One of Chicago's quainter neighborhoods, Ravenswood has a number of historic homes, including the onetime residence of formerly incarcerated ex-Governor Rod Blagojevic! It's also convenient to a couple of other popular dining and shopping neighborhoods, Andersonville and Lincoln Square, if you don't mind a short drive or a longer walk.
FOOD
Farm Bar
1970 W. Montrose Ave. (8 min walk)
This aptly named, Midwest-focused restaurant actually does operate a farm that supplies them with produce and honey (the farm houses 40 beehives) that makes its way into cocktails, often made with local spirits. The menu leans towards the simple and comforting, and their cheese curds are some of the finest you'll find this side of the Wisconsin border.
BienMeSabe
1637 W. Montrose Ave. (5 min walk)
A Venezuelan cafe whose arepas have developed a following among several Latin American members of the Chicago White Sox, BienMeSabe also serves excellent empanadas, ceviches, and other favorites. They're BYOB, and a couple of arepas and a six pack makes for an outstandingly cost-effective dinner for two.
Spacca Napoli
1769 W. Sunnyside Ave. (4 min walk)
Spacca Napoli has been a Chicago favorite for decades when locals are craving a pizza vibe that leans more Naples than North Side. Always peruse the specials, as there will often be a couple of interesting selections channeling seasonal flavors, but the staple pistachio cream pizza topped with sausage and basil is also a can't miss.
BOOZE
Ravenswood Tavern
1829 W. Montrose Ave. (3 min walk)
The kind of unassuming neighborhood bar that represents a quintessential Chicago experience, this cash-only corner bar is the kind of place you post up for an afternoon, throw some money at the jukebox, throw some darts, throw back some Malӧrt, and throw… you get the idea.
Carol's Pub
4659 N. Clark St. (19 min walk)
Full disclosure: this legendary honky tonk (entering its sixth decade) is best experienced after midnight—many a hungover Chicagoan has explained their bleary-eyed state the next morning by simply muttering "Carol's". But it's a genuine local institution any time you stop in even if it's just for some afternoon country music paired with a cold one and a char dog.
COFFEE and CANNABIS
Spoken Cafe
1812 W. Montrose (3 min walk)
A Chicago coffee shop with a Cajun accent (both owners have Southern Louisiana roots), Spoken rotates through different single-origin coffees from local roasters, makes an outstanding bagel breakfast sandwich, and ships its jams, pickles, and even its boudin links nationwide if you taste anything you like.
Chicago Cannabis Company
4009 N. Damen Ave. (15 min walk)
See previous writeup. They didn't pay a sponsorship fee. They're just well-situated geographically.
OTHER POINTS of INTEREST
Graceland Cemetery
Enter at Montrose & Clark (20min walk)
A great place to either enjoy a quiet walk or creep yourself out, depending on time of day, Graceland is the final resting place for many a noted Chicagoan (anyone who read Devil in the White City will recognize the names Daniel Burnham and Allen Pinkerton). There's also the gravesite of Inez Clark, featuring a well-preserved statue of a child encased in glass that has inspired many a ghost story and sighting.
Malt Row
Locations and travel times vary
In full transparency the "Malt Row" label was coined a few years back by the Ravenswood Chamber of Commerce, but the area does offer an unusual density of standout breweries and distilleries. A few highlights: Dovetail, Half Acre, Koval (this is particularly close to the venue), Hop Butcher and Spiteful.
BOOT CAMP VENUE
2105 N. Elston Ave.
Note: Horween sits along the border between Chicago's Lincoln Park and Bucktown neighborhoods, so there are options here drawn from both. The immediate area around Horween isn't the MOST walkable, so you may choose to opt for a rideshare, but these establishments are all within a reasonable stumble.
FOOD
Pequod’s
2207 N. Clybourn Ave. (9 min. walk)
Known for its addictive caramelized cheese crust, Pequod's has been a neighborhood staple since pizza iconoclast the late Burt Katz opened it in 1970. Style-wise it falls somewhere between Detroit style and classic Chicago deep dish, giving it a unique niche in the Chicago pizza canon that has won it legions of fans.
Choppers
1659 N. Ashland Ave. (11 min walk)
This retro-style fast food staple serves solid renditions of Chicago classics (red hots, Polish sausage, Italian beef), as well as their trademark Choppak (the "adult happy meal" as they call it), a double burger with fries and coleslaw, and, for some reason, no toy?
Anor
1450 W. Webster Ave (8 min walk)
For those seeking something a bit different, this Uzbek restaurant specializes in Central and Eastern European favorites (try the manty, a hearty beef-filled dumpling). The tandoor-baked samsas will feel familiar to samosa lovers, and the honey cake is a standout for anyone looking for a blood sugar spike.
BOOZE
Lottie's Pub
1925 W. Cortland St. (15 min walk)
Having celebrated its 90th year in business in 2024, some may recognize Lottie's as the real-life filming location of "Molly's" in the TV show Chicago Fire. Dick Wolf's seal of approval aside, it's a classic Chicago tavern (check out the antique coolers behind the bar) with a solid lineup of no-frills bar food, plentiful flatscreens for sports fans, and the regal distinction of being one of the top sellers of Coors Banquet in the country.
The Albion Manor
1480 W. Webster St. (7min walk)
Relatively new to the neighborhood, this bi-level British pub is a go-to for upticked takes on pub staples like fish and chips or curry fries. The beverage options run the gamut from a well-curated tap list split between imports and American craft favorites, a well-priced wine selection, and a mix of classic and signature cocktails, though the Pimm's Cup suits the ambiance particularly well.
Floriole Cafe & Bakery
1220 W. Webster Ave. (15 min walk)
Serving locally roasted Metric Coffee, Floriole started out selling pastries at Chicago's Green City Market before setting up shop permanently in this welcoming corner bakery (the sunlit second floor is an excellent place to post up). So come for the caffeine fix, but don't sleep on the baked goods.
COFFEE and CANNABIS
nuEra
1308 W North Ave. (15 min walk)
This Illinois-only mini chain of dispensaries operates eight locations statewide, but this is their only Chicago store. Expect a helpful staff, an efficient online ordering operation, and a bevy of cannabis options to suit any preference.
OTHER POINTS of INTEREST
Whirlyball
1825 W. Webster Ave (10min walk)
A mashup of lacrosse, basketball, and … bumper cars, Whirlyball is a Midwest standby for company outings, birthday parties, and anyone looking to just unleash some aggression. If you work up an appetite, there is a perfectly adequate bar and grill on premises as well. If you think you might be interested, consider booking ahead of time.
The Green
2131 N. Elston Ave. (5min walk)
November golf outings in Chicago aren't typically an option, but The Green is an approachable, state-of-the-art golf simulator for all seasons. Though they do accept walk-ins, reservations don't hurt. That said, if you find yourself having to wait your turn, you can always kill time at the bar mowing through some hot honey wings while watching other regular non-professionals golf. Thrilling!
BOOT CAMP VENUE
1515 W. Carroll Ave.
Note: The Tannery Row sits on the edge of Chicago's West Loop (and the more recent real estate developer-named Fulton Market District). It's one of Chicago's restaurant hotbeds, particularly for fine dining, so there’s a huge array of options in the area.
FOOD
Maxwell's Trading
1516. W. Carroll Ave. (1 min walk)
One of the most celebrated Chicago restaurant openings of last year, Maxwell's Trading is one of those restaurants where the culinary point of view is tough to pin down (though Japanese, Italian, and Thai influences are common themes), the menu changes frequently, and everything just seems to work. Reservations highly recommended.
The Loyalist
177 N. Ada St. (9 min walk)
If you want to experience the upper crust of Chicago's fine dining scene, The Loyalist's upstairs sister restaurant, Smyth, recently earned its third Michelin star. But don't sleep on the more casual basement dwelling sibling, a zero pretense candlelit haunt with an eclectic cocktail program and a celebrated burger that can go toe-to-toe with the neighborhood's more hyped Au Cheval without the inconvenience of a three-hour wait (though a reservation wouldn't be a bad idea).
Tempesta Market
1372 W. Grand Ave. (12 min walk)
Anyone who appreciates a good sandwich, particularly an Italian-leaning one, will find this area to be a goldmine (neighborhood icon J.P. Graziano is just a slightly further trek). Tempesta is a more recent addition where you'll find The Dante (basically an Italian sub with giardiniera and ndjuja aioli), hanging out with a wagyu pastrami reuben and a Cubano that could hold its own just fine in South Florida.
BOOZE
District Brew Yards
417 N. Ashland Ave. (5 min walk)
You could absolutely get your beer fix at the nearby Goose Island Tap Room, but also consider this pour-your-own collective of nanobrewers as an alternative. The styles run from classic to boundary-pushing and the food is provided by Chicago favorite Lillie's Q, a Chicago smoked meat favorite from a two-time Memphis in May winner.
The Aviary
955 W. Fulton Market (16 min walk)
If you want to experience a taste of Chicago culinary legend Grant Achatz but couldn't get an Alinea reservation, consider his inventive cocktail concept, Aviary (reservations still recommended, but easier to come by). The cocktails unsurprisingly register at a relatively high price point, but there's an unmatched level of craft and artistry that makes it feel worth it. If that's not high end enough, their no-longer-a-secret speakeasy The Office offers an even more exclusive experience.
COFFEE and CANNABIS
Drip Collective
172 N. Racine Ave. (14 min walk)
Part cafe, part art gallery, part music venue, and part pop-up pizzeria, the constants at Drip Collective, which joined Chicago's coffee scene last year, include meticulously crafted coffee drinks and a space buzzing with creativity. The wooden bleacher-style seating (along with regular, you know, tables) adds to the space's community-minded feeling.
Dispensary 33
1152. W. Randolph St. (15 min walk)
Chicago's first licensed cannabis dispensary (back in the medical-only days during which many Chicagoans experienced a sudden uptick in general anxiety), Dispensary 33 is an incredibly well-run operation with a vast selection and a staff that is as informed and passionate as any in the city, though you can also order ahead if you aren't looking for too much human interaction.
OTHER POINTS of INTEREST
Cobra Lounge
235 N. Ashland (4 min walk)
The Cobra Lounge is a venerated Chicago institution for underground rock shows, often leaning towards punk, hardcore, metalcore, and various other cores. Even if there's not a show going on, it's a strong low-key stop for a beer (the venue also serves as home to All Rise Brewing Co.) and one of the city's most perpetually underrated burgers.
United Center
1901 W. Madison (20 min walk)
Even if the stars don't align to catch a Bulls or Blackhawks game (though they might!), you can still take a stroll past the house that Jordan built, pay quick homage to the statue, and make a purchase at The Madhouse, the team store for both franchises that stays open and moving merch whether it's a game day or not.
BOOT CAMP VENUE
3717 N. Ravenswood Ave. #113
Note: The Chicago School of Shoemaking sits on the edge of Chicago's Lake View neighborhood, though it's far enough northwest to be reasonably removed from the debauchery of Wrigleyville (though not THAT far, if that's your thing).
FOOD
Tango Sur
3763 N. Southport Ave. (13 min walk)
A BYOB Argentinian steakhouse that has been feeding Wrigleyville some of the best-tasting beef for its price point in Chicago for decades, Tango Sur also stands out for its addictive chimichurri, flaky empanadas, and housemade morcilla. Scoop a few bottles of red at one of the nearby grocers and have yourself a feast.
The Diner Grill
1635 W. Irving Park Rd. (11 min walk)
Open since 1937, this 24-hour diner car and greasy spoon (for real, they’ve had to shut down due to a grease fire on more than one occasion) is a go-to for shift workers and late night revelers, but it gets the job done any time of day. If you're feeling adventurous, try the iconic "Slinger," a massive helping of eggs, hash browns, cheese, and burger patties covered in chili. Or get the off-menu "Dick Burger" (basically a bacon cheeseburger with grilled onions, hash browns, and a runny egg) that a line cook from triple-Michelin-starred Alinea allegedly created by request one late night after work.
Coalfire
3707 N. Southport Ave. (11 min walk)
Chicagoans bristle at the notion that they're strictly a deep dish town partly because of the existence of places like Coalfire, which turns out oven-charred pizzas with a "quality over quantity" approach to toppings that has won a devoted following (this is actually Coalfire's second, more expansive location). It's hard to make a bad call, but the Berkshire sausage with nduja whipped ricotta and Calabrian chile is tough to pass up.
BOOZE
The Long Room
1612 W. Irving Park Rd. (11 min walk)
Doubling as an excellent coffee shop during the morning hours, The Long Room is one of Chicago's most beloved beer bars, always keeping a fresh and interesting selection on their dozen taps, with plenty more ammo in the cooler. More recently, they've added an equally well-run cocktail program and a rotation of chef partners offering different brunch or dinner menus depending on the day you show up.
The Globe Pub
1934 W. Irving Park Rd. (12 min walk)
If you happen to have a soccer match or other international sporting event you are concerned you'll miss, the Globe is your spot. Entering its third decade, it's particularly abuzz during large international tournaments, but you'll find fans invested in some match you may or may not have known was happening just about any day of the year. The beer list tends to lean European, and the Scotch eggs are an elite bar snack.
COFFEE and CANNABIS
Loba Pastry & Coffee
3600 N. Lincoln Ave. (5 min walk)
Loba is a cozy shop with friendly baristas and excellent espresso drinks courtesy of North Carolina-based Little Waves coffee, but you'd be remiss if you only caffeinated here and missed out on the inventive work of James Beard-nominated pastry chef and owner Valeria Socorro Velazquez Lindsten (think mole croissants, cheese-lined kouign amman, and curry white chocolate scones). Don't miss the Emmie, a crusty outside, custardy inside creation that resembles a donut-shaped canalé. It thankfully never comes off the menu.
Chicago Cannabis Company
4009 N. Damen Ave. (11 min walk)
This Chicago-based dispensary with two locations also has its own in-house product line (though they carry most other staples as well). And if you should forget to make a stop, they also offer same-day delivery on select products via DoorDash.
OTHER POINTS of INTEREST
Wrigley Field
1060 W. Addison Rd. (25 min walk)
Baseball season may be over, but the home of the Cubs / Elwood Blues never sleeps. If nothing else, you can grab a photo in front of the iconic red Marquee and the Harry Caray statue before roaming the neighborhood and popping into any of its many watering holes. Most of the neighborhood has turned over amid a surge of Ricketts family-led real estate development, but if you want a true classic that predates all that, try Sluggers (upstairs batting cages), Murphy's Bleachers (the OG), or The Gman Tavern (live music).
The Music Box Theatre
3733 N. Southport Ave. (14min walk)
A neighborhood landmark since 1929 and a staple for cinephiles, The Music Box hosts everything from vintage classics to 70mm screenings of new releases to live events that may or may not even use screens. Give their calendar a glance and see if they're running anything that fits your taste and schedule.
BOOT CAMP VENUE
2439. Elston Ct.
Note: While these establishments are all reachable within the listed walk times, Ashland Leather's highway-adjacent location doesn't always make for the most scenic or simple of walks, so you may want to opt for rideshares instead. If you're willing to ride a little further into nearby Logan Square, you'll find one of Chicago's best eating and drinking neighborhoods, with far too many excellent options to list here. Also, many of the Horween recommendations are convenient from Ashland Leather, as the two are relatively close together.
FOOD
Leavitt Street Inn & Tavern
2345 N. Leavitt St. (15 min walk)
A classic Chicago tavern that actually does operate a small inn upstairs if you need to crash, Leavitt Street has actually developed a bit of a culinary following in recent years thanks to a much-lauded smashburger (though don't sleep on the fried chicken sandwich, either). Pair it with whatever pour catches your eye from their Midwest-focused tap list.
Chef's Special
2165 N. Western Ave. (20 min walk)
From the team behind Giant, a beloved restaurant that isn't near any venues but is absolutely worth your time, Chef's Special offers riffs on Chinese takeout classics paired with elevated cocktails and a throwback mid-century aesthetic. The lightly fried walnut shrimp and Thai chili and Sichuan peppercorn-spiced dry chili chicken are a couple of crowd favorites.
Birria Estilo Jalisco
2230 N. Western Ave. (20 min walk)
Many out of towners don't realize that Chicago is one of best cities in the U.S. for Mexican food (the only city with a larger population of Mexican immigrants is Los Angeles). Birria Estilo Jalisco is one of many small restaurants dialed into a specific regional specialty, in this case Jalisco-style birria, which they have been stewing in huge, fragrant batches since well before quesabirria tacos started dotting the menu of every overpriced sports bar in the country. That said, they'll gladly serve you some of those if you wish.
BOOZE
The Charleston
2076 N. Hoyne (12 min walk)
On the surface, this place looks like yet another of the aforementioned classic Chicago taverns, but The Charleston brings a little bit more to the table than the average corner joint. You can count on the bartenders here to flawlessly execute a classic cocktail (not a recommended expectation for all neighborhood taverns), and you can expect an energetic late-night scene featuring a rotating cast of DJs.
Web Pub
2026 W. Webster (9 min walk)
The building that houses Web Pub has been slinging drinks under a few different names since 1947. The current iteration continues the space's legacy as an unassuming and welcoming dive bar, with notoriously friendly bartenders, cheap beer, semi-maintained dartboards, and zero pretense.
COFFEE and CANNABIS
Allez Cafe
2239 N. Western Ave. (20 min walk)
A relatively recent addition to the neighborhood with more culinary cred than your typical coffee shop (the owners have Chicago fine dining legends like Alinea and Blackbird on their resume), Allez Cafe delivers on the coffee and pastry front, but the true star is their social media darling breakfast sandwich. It consists of a custardy egg square topped with a crispy hash brown patty, bacon, onion aioli, and jalapeno jam, all held together by a soft potato roll. It draws big lines in the morning, and it's worth the wait, but you can also order takeout ahead of time.
Village Dispensary
1850 W. Webster Ave. (5 min walk)
Village offers the typical assortment of cannabis products, including their own house brand, plus an online ordering interface supported by an AI-driven "virtual budtender" if you're truly decision-challenged.
OTHER POINTS of INTEREST
Logan Arcade
2410 W. Fullerton Ave. (24 min walk)
With a more robust library than your average arcade bar (try the 10-player behemoth Killer Queen if you're uninitiated), Logan Arcade has a particularly deep pinball selection, a strong beer list, and their own in-house vegan hot dog concept called Fry Like an Eagle. Truly, there's something for everyone.
Kanya Lounge
2525 N. Elston Ave. (25min walk)
Axe throwing? Check. Rage rooms? Check. Billiards? Check. Kanya is a two-story grownup playground where you can spring for bottle service, hurl some axes around (well, at one specifically marked wall), and take out some aggression if need be. Call ahead for reservations if you have an eye on a particular activity.
