This Rooftop Bar Makes the Biggest Ice Cream Sandwiches & Cocktails
1. Fried house-made bologna sandwich
This isn't your childhood "slice of cold bologna and Kraft singles slapped between two pieces of Wonder bread" lunch box sandwich (if you can even call that a sandwich). You're not gonna want to trade this far-from-basic, cheesy, meaty, salty deliciousness piled high on the softest buns for anything -- not even for your friend's insanely good burger.
2. Cemita Atomica
Logan Square, West Loop
This family-owned sandwich shop puts its own spin on traditional cemitas hailing from Puebla, Mexico, and the Cemita Atomica is our top pick (mostly because it throws in a little bit of everything). A trio of glorious meats -- Krakus ham, guajillo-rubbed pork loin, and breaded pork milanesa -- are layered with smoky chipotle peppers, fresh avocado, and hand-pulled Oaxacan cheese. Even the slices of sesame-topped egg bread are specially spread with smoky chipotle salsa beforehand.
3. Sausage biscuit
Make no mistake, Bang Bang's small-batch sour cream biscuits are every bit as legendary as their sweet, just-baked pies. When you stack their fluffy, buttery goodness with ginger-sage sausage, sawmill gravy, seasonal jam, and a poached egg, you've got a crazy-flavorsome combo. With a second location in Ravenswood in the works, getting your hands on the notorious pie shop's savory biscuit sandwiches (and, oh yeah, those heavenly pies) just got easier for breakfast, lunch, AND dinner.
This Costa Rican spot dishes out mouth-watering pepito sandwiches. Your biggest decision will be whether to indulge in the ribeye steak or the chicken, which'll then be covered with sautéed onions, seasoned black beans, and gooey Muenster cheese on French bread, and drizzled with brown Lizano sauce.
5. Torta ahogada
River North, Wicker Park
There's a reason the dine-in only torta ahogada is the most-ordered menu item at Rick Bayless' casual Mexican eatery: it's the king of tortas, regally presented in a shallow bowl of tomato-árbol chile broth. When continuously dunked into the earthy sauce, crispy bolillo rolls filled with golden hunks of pork carnitas, black beans, and pickled onions can turn into an immensely satisfying drippy carnage, so have a napkin handy.
6. Fatso's Po'Boy Challenge
While the Double Fatso with cheese at this fast-food joint is a go-to staple, the real crowd-pleaser is one of its namesake (truly ridiculous) food challenges. What bucket list would be complete without a big-ass sandwich and the potential to win at life? House this 7lb bad po-boy (2lbs of which are fried jumbo shrimp), a pound of fries, and a 32oz soda in 45 minutes or less, and you've got yourself a comped meal, $50 gift card to Lockdown Bar & Grill, your name on a shiny plaque, and a new T-shirt!!
7. Three Little Piggy
Anthony Bourdain deemed the railway-car-turned-diner's gut-busting sandwich "the greatest sandwich in America." With a deep-fried breaded pork tenderloin cutlet, double-smoked ham, bacon, two huge onion rings, and melted Gruyere cheese, topped with two fried eggs on a brioche bun, it's probably also "the greatest hypertension-causing sandwich in America." But we're firm believers in factoring some risk into a sandwich bucket list.
8. Mr. G
The third-generation Italian wholesaler and grocer touts one of the finest subs in the city. When you ask for the Mr. G house specialty, primo ingredients like sharp imported provolone, hot sopresatta, prosciutto, and salami are piled onto crusty, coal-fired bread from D'Amato's Bakery. It's topped with a truffle mustard balsamic vinaigrette, hot oil, marinated artichokes, fresh basil, and lettuce mixed with red wine vinegar and oregano for an off-the-charts sub experience.
10. Italian beef sandwich
You could arguably have a whole separate Italian beef bucket list, but the original purveyor of the city's iconic sandwich on Taylor St (which is a different company from the franchises) is a good place to start either way. Get it "dipped wit hot and sweet," then check it off your list. Repeat as needed.
This walk-up food stand looks like it's about to collapse, but it's got a loyal following for its David Berg kosher-style dogs. And it's one of the few places you can still find the legendary Chicago sandwich: the Mother-in-Law, which is basically a Chicago-style dog with a chili and cheese-topped tamale in a bun instead of a hot dog, along with the traditional fixings, including cucumbers.
12. Breaded steak sandwich
This family-owned Bridgeport staple serves up an authentic breaded steak sandwich (maybe not the best sandwich in the entire world but certainly very very good). Get your king size order covered with gooey mozzarella, hot giardiniera, and sweet peppers, then prepare for a night on the couch.
13. Grilled spicy shrimp and fried oyster po-boy
Typically, you'd have to choose between the shrimp or oysters for a sandwich, but this friendly organic spot loads copious amounts of both grilled spicy shrimp and perfectly fried oysters -- along with a zesty cajun mayo and house-made giardiniera -- onto a hearty baguette.
14. BBQ pork bánh mì
Lincoln Square, Uptown
This Vietnamese bakery churns out solid bánh mì options with all the fixings that make it a welcome departure from the standard lunchtime sub. The BBQ pork sandwich with crisp cucumber spears, sweet pickled daikon, shaved carrots, jalapeños, and fresh cilantro in a crusty baguette is a stand-out special. It's not always easy to find a table in either of their tiny, storefront locations if you're dining in, but it's well worth the wait.
15. Falafel sandwich
Crunchy, garlicky falafel is the name of the game at this Middle Eastern standby. The fryer-fresh falafel balls are still moist enough on the inside to not to completely crumble all to hell within their soft pita shell. Plus, they pour tahini sauce throughout the pita pocket, not just on top, so the entire sandwich is flavorful, even with simple embellishments like lettuce and tomato.
16. Corned beef sandwich
This small, old-school diner with warm staff behind the counter has been serving the working class community since 1933. They've got some award-winning grits and eggs, and definitely don't skimp on the juicy, freshly cut corned beef when it comes to their signature sammy, which is probably why they have such a devout following.
18. Steak sweet sandwich
This South Side steak staple since 1969 was recently shuttered by a fire, but still managed to get back up and running at a new location next door. It's continued serving sandwiches like the ultra-famous "steak sweet," a South Side take on a steak sandwich on a Gonella bun with coarsely-chopped steak and peppers. Just ask for the "Steak sweet, fries with sauce."
19. Wood oven roasted pig face
You might have to wait months to get it, but this place fires up the oven for a true farm-to-table delicacy with tantalizing textures. Resting atop a tamarind vinaigrette and cilantro oil drizzle, two tender pig face patties sandwich in a layer of crispy potato sticks, then it's all topped with a maple gastrique, and, naturally, a runny egg to make breaking into the first bite even better.
The Loop, South Loop
While the Cubano is a star at the popular lunchtime cafe, you'll also find the Uruguayan specialty that's hard to come by in this city -- the chivito. The steak is marinated in a homemade mojo for at least a day before it's sandwich-ready... that is, before the onslaught of ham, bacon, fried egg, mozzarella, lettuce, tomato, onion, and citrus mayo are also crammed between sturdy loaves.
21. Lucky's Challenge
Lakeview, Wicker Park
Why opt for just one Pittsburgh-style hulk sandwich with fries and coleslaw in it when you could have THREE stacked with different kinds of deli meats? Devour all three overstuffed sandwiches within an hour, and all of 'em are on the house and your pretty mug will live on wall of fame style, which is just as cool as doing it for Man v. Food, right?
We can't seem to get enough steamed mussels and crispy frites at this Belgian brew house (it's a dish to eat before you die, after all), but the friendly neighborhood mainstay also boasts one of the most craveable sandwiches in the city. With its house-made cashew butter, fig jam, and melted raclette cheese paired with pan-fried sourdough crusts, their PB&J upgrade is one of the smartest orders you'll make, so long as you keep the beers coming.
23. Steak jibarito
Initially created at Juan "Pete" Figueroa's Humboldt Park resto, Borinquen, the Puerto Rican-inspired dish (pronounced hee-bah-ree-to) consists of two thin planks of flattened and fried green plantains in lieu of bread, which are still strong enough to hold all the grilled steak, lettuce, tomato, mayo, and melted cheese you can handle.
24. Roasted pork jibarito
The original Borinquen in Humboldt Park may have closed since it gave Chicago its first taste of the addictive jibarito, but rest assured you'll find a solid version of the sandwich with roasted pork with homemade hot sauce here too... good, garlicky, and greasy mmmhmm.
25. Meatball sub
Formento's grab-and-go counterpart serves casual Italian-American dishes like a hearty signature meatball sub. The made-to-order sandwich features gargantuan, house-made meatballs covered in marinara, mozzarella, and giardiniera nestled inside a crusty baguette.
26. Ham and raclette panino
The traditional ham and cheese sammie goes upscale with Lula's panino. They combine smoky cured ham and oozing raclette cheese with radish, fresh salad greens, pickled onion garnish, and black currant mustard on a crusty ciabatta bun. Topped off with a fried farm egg, the rich elements come together in sweet-and-salty bursts that are worth savoring.
27. Hamburger sandwich
Primarily lauded for its rotisserie duck, Kevin Hickey's well-received menu also features a classic patty melt sandwich that consists of a square Tallgrass Beef patty, farm fresh Brun-uusto cheese, onions, and dijonnaise on buttered rye bread -- and it all goes on the grill at the same time. Plus, you can get it piping hot at the bar, so even if you can't get a table, you can still go home with a happy belly.
28. Oaxacan pork sandwich
Known for its original sandwiches and fresh-baked bread, this cash-only counter-service cafe crafts a mean Oaxacan pork sandwich. The pork chop sandwich has an authentic Mexican sweet and spicy flavor between crusty, homemade bread. For the same price as Subway, the generously portioned, top-notch handheld that could easily make two meals reigns supreme as a quick and tasty option.
29. Toasted pimiento cheese
If their fried chicken is any indication, this place does Southern food right. Satisfy your soul with a melty grilled cheese sandwich on marbled rye that's got a real kick thanks to the Worcestershire sauce and local heirloom pimientos melted right into the cheddar.
30. Wild Boar Sloppy Joe
The Michelin-starred gastropub takes the Sloppy Joe to another level with spicy ground boar, peppery pickled jalapeños, crispy sage, and onions on a toasted, house-made bun. We dare you not to use any silverware to catch any rogue wild boar bites.
31. The Fairfax
The Loop, West Loop, Food truck
Savory breakfast sandwiches, especially if you can find them "after hours," are the cure to just about anything. A Monday morning, a hangover lingering into late Sunday afternoon, a breakup, watching presidential campaign coverage... anything. Fresh egg sammies like The Fairfax, with its Egmont cheese, sautéed bell peppers, wilted spinach, and house green goddess sauce on a seven-grain roll, will power you through whatever it is that ails you.
32. Gym Shoe Sandwich
The Pakistani-run sub shop on the South Side serves an underrated signature Chicago sandwich, which has a beautiful combo of meats -- roast beef, corned beef, and gyro meat -- plus lettuce, tomato, mustard, mayo, cheese, and tzatziki sauce served in a Philly cheese steak-style bun. Plan on taking your meals to go from the walk-up counter space.
33. Greek Squeeze
Family owned and operated since 1948, George's offers traditional homemade Greek and American favorites. Their extensive menu includes everything from hot dogs and burgers to Italian beef and Philly steaks to gyro and Grecian chicken and salad selections. The "Greek Squeeze" gyro sandwich is essentially a sub stuffed with gyro meat and topped with melted cheese, grilled onions, tomatoes, and the house-made tzatziki. You won't have to worry about your next meal for days after polishing one off.
35. Liverbest Sandwich
Gene's rooftop beer and wine garden is undoubtedly one of the best summer drinking spots in the city, but sitting atop the butcher shop has advantages beyond a killer outdoor hangout space... like grilled German sausages and pretzel sandwiches with all kinds of meats. For their "Liverbest Sandwich," they'll throw a thick slab of creamy liverwurst with some sliced pickles on a pretzel roll, so it's prepped for you to slather on one of the assorted mustards and wash down with a pilsner.
37. Pork belly pastrami sandwich
The pork belly pastrami sandwich -- thick slices of 10-day cured and 12-hour smoked bacon-to-be piled on a brioche bun -- is the melt-in-your-mouth deliciousness you'll be ordering at the counter of this no-frills BBQ joint. Meaty, fatty, and smoky with a little pastrami spice crust makes for one hell of a sandwich. In fact, we don't even think you need to pair it with any of the fine sauces offered: molasses-based Sweet & Sticky, vinegar-y Tart & Tangy, or Wicked Spicy.
38. Spicy chicken sandwich
Lakeview, River West
Head to The Roost, a food truck with a permanent BYOB storefront on Irving Park Road, for Carolina-style recipes like crispy, spicy fried chicken on a flaky buttermilk biscuit topped with dill pickles, coleslaw, chipotle buttermilk ranch, and cheddar or blue cheese. Heat things up even more by ordering the Nashville Hot, Habanero BBQ, or Buffalo variations. Creamy mac and cheese and sweet peach cobbler round out the feast.
39. Pork chop sandwich
University Village/Little Italy
The stand-up only Polish sausage sandwich stand dating back to the old Maxwell St in the 1930s grills bone-in pork chops to a sizzle and serves them on hot buns with layers of yellow salad mustard, mounds of sweet Spanish onions, and spicy peppers. They're irresistibly tender and tasty, and a bag of fries is thrown in for free.
40. Porchetta sandwich
Wicker Park's hybrid butcher shop/eatery/salumeria serves up stand-out, meat-oriented American fare such as the deli's Porchetta sandwich, a house-made pork loin wrapped in pork belly with asiago, arugula, apricot marmalade, and tomato on your choice of 7in or 12in French, white, or wheat bread.
Sign up here for our daily Chicago email and be the first to get all the food/drink/fun in town.
Nicole Bruce is a contributing writer for Thrillist. She thinks there's gotta be more to life than sandwiches, but there can't be much else. Find her on Twitter at @nicoleabruce.