How to Eat and Drink Your Way Through Downtown Chicago in a Day

Chicago is a large city and can’t be fully experienced in a single visit. But for travelers here for a day, it’s a struggle to get away from downtown and see other neighborhoods. Finding rib tips and other under-the-radar delights may have to be saved for another visit. But to ensure visitors get a more balanced taste of downtown Chicago, ignore those hot takes from coastal elites and follow this 24-hour itinerary.

8 a.m. — Breakfast at Lou Mitchell’s, 565 W. Jackson Boulevard

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Lou Mitchell’s is one of the last few dives in Chicago, an incredible diner experience since 1923 with free doughnut holes and Milk Duds. Yes, this is the cliched “slice of Americana” boomers romanticize, with a vintage counter, narrow quarters, and the ‘60s menu of pancakes, bacon, and eggs. The restaurant executes the classics with great poise, and the dining room feels comfy with folks from all walks of life patronizing the space.

11 a.m. — Drink at the John Hancock Center, 875 N. Michigan Avenue

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The John Hancock Center, with its twin antennae, often gets mistaken for its similar-looking sibling, the Willis Tower. The Hancock also offers gorgeous views of the city, but visitors won’t have to pay an admission fee like they do at the former Sears Tower. The Signature Lounge at the 96th features a full bar, light snacks, sandwiches, and desserts. Expect to pay around $20 for the specialty cocktails. The rotating beer from local breweries like Revolution and Three Floyds may be the best bet.

Noon — Italian beef from Al’s Beef, 548 N. Wells Street

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Skip Portillo’s — it feels too much like a tourist trap. With apologies to The Bear, which took inspiration from the stand, skip Mr. Beef — the giardiniera, Chicago’s signature pickled veggie medley, is bland. Al’s Beef is another chain that continues to deliver the best beef and fresh-cut fries (so underrated) within downtown’s limits. Don’t despair, the downtown location recently moved down the street.

1:30 p.m. — Lunch at Avli on the Park, 180 N. Field Boulevard

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Lakeshore East, a somewhat hidden neighborhood near Navy Pier, is near Millenium Park and a great escape from crowds. While taking a walk, stop at Avli on the Park, part of a Chicago mini-chain of Greek restaurants. Enjoy light bites like gyros, sandwiches, and bowls. The gyros cone was invented in Chicago, distributed to street food stands all across the city. Avli doesn’t use the cone, and instead puts together their own elevated version without the elevated price.

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3 p.m. — Pick up a half-baked or frozen pizza from Lou Malnati’s, 439 N. Wells Street

Lou Malnati’s

If travelers are on a strict schedule, don’t waste precious time waiting for Chicago-style deep-dish pizza. It’s dense and magical, despite the cliched chorus from out-of-town (and local) edge lords who refuse to call it pizza. But more relevant than those hot takes is the reality that it takes around 45 minutes to bake a pie. Pick up a prepackaged frozen pizza or better yet, call ahead and order a half-baked pie. Wrap it with plastic, bring an insulated bag, and take it home to enjoy after the trip. Lou’s also serves up Chicago thin-crust pizza, and it would be a power move to order a small and try one out.

4:30 p.m. — A drink at Miller’s Pub, 134 S. Wabash Avenue

Miller’s Pub/Facebook

After dropping that pizza off in a fridge, it’s time to get back to business. Hear the buzz of the train as you enter Miller’s Pub, where Chicago style isn’t a cliche. Does the space have character? Tons, with photos and trinkets covering the walls. This is a big city bar with friendly professional bartenders who can regale travelers with stories. The pub menu is venerable from burgers to ribs. Order a Tom & Jerry, a house specialty, especially during wintertime.

7:30 p.m. — Dinner at Obelix, 700 N. Sedgwick Street

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Located a little north of the Mag Mile, Obelix is a delight, run by a pair of brothers whose parents owned several of the city’s most popular French restaurants. This is a French restaurant done “Chicago style,” which is a term often poked fun of by outsiders, but to put it bluntly, it’s a democratized restaurant where several voices come together to produce chic food, like a foie gras taco, that presents elevated ingredients in recognizable form. French food traditionalists may scoff, but from beautiful beef Wellington to dry-aged duck, Obelix, a James Beard Award finalist, is a delight.

10:30 p.m. — Drinks at Bar Sotano, 443 N. Clark Street

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Rick Bayless took the basement underneath his River North complex and created a restaurant where the cocktails shine. Bar Sotano is a laid-back spot with a variety of mezcal cocktails inspired by Rick and Deann Bayless’ travels. Some are just absurd with a drink based on taco al pastor. The profiles a fruity, spicy, and unlike any bar in the world. Fun small bites, tacos, and even a burger are available.

Midnight — Drinks at Rossi’s, 412 N. State Street

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After going upscale at Cindy’s, head over to one of downtown’s last true dive bars. Rossi’s is one of the most unique places in the city. Beer bottles are stored in the coolers in the back. It’s an impressive selection giving tourists and locals a strong variety of local beer. Grab a bottle and pay for it at the bar. This dive draws one of the most eclectic crowds including concertgoers from the House of Blues next door, business folks working the Loop, and awkward tourists unsure what to expect.

1:30 a.m. — A late-night snack and some sass at Wiener’s Circle, 2622 N. Clark Street

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Most Chicago bars close at 2 a.m. For those still standing, there’s one quintessential Chicago thing that needs to be checked off the list. Head to Wiener’s Circle for a side of sass and wait in line for the classic Chicago hot dog dragged through the garden with pickle spears, sliced tomatoes, diced onions, green relish, sport peppers, mustard, and celery salt. Don’t order ketchup. Don’t ruin this perfect day.