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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 except from the city’s skyscrapers. 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. — Doughnuts from Aster Hall, 900 N. Michigan Avenue
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Doughnut Vault is one of Chicago’s best doughnut shops. Instead of fighting lines at the vault’s two locations, walk into this food hall at 900 N. Michigan Avenue and order a pastry from 3 Greens Market. The booth is run by the same folks behind Doughnut Vault, and customers can grab a treat and coffee.
- The 17 Essential Doughnut Shops in Chicago [ECHI]
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, 169 W. Ontario Street
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Chicago-style Italian beefs are one of the city’s greatest treasures, born from an immigrant’s tale of needing to make a cut of beef last to feed large families at gatherings. Al’s is one of the best in the business with thinly sliced beef and fresh-cut fries. Customers can also opt for the combo, an Italian sausage topped with the beef. Be sure to specific hot or sweet peppers. The sandwich can also be order with wet (extra jus) or dry (sans jus). Consider this an appetizer for lunch.
- Chicago’s 20 Essential Italian Beef Sandwiches [ECHI]
1:30 p.m. — Lunch at Pacific Standard Time, 141 W. Erie Street
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Resist the urge to walk inside the futuristic giant McDonald’s across the street and grab a seat at Pacific Standard Time, one of Eater’s Best New Restaurants for 2018. It was also Eater Chicago’s Restaurant of the Year in 2018, thanks to eclectic West Coast-style cooking. There’s a little bit for everyone in this fun space guided by gifted chef Erling Wu-Bower’s imagination. Find top-notch pita surrounded by accoutrements, Pan Asian chicken wings, and more. One Off Hospitality Group, responsible for the Publican and others, is a partner in the restaurant. At 3 p.m., the restaurant’s rooftop spot, the Laurel Room, opens. So it may be worth staying a bit.
- River North’s Pacific Standard Time Makes 2018’s Best New Restaurants List [ECHI]
3 p.m. — Pick up a half-baked or frozen pizza from Lou Malnati’s, 439 N. Wells Street
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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) edgelords 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. Either 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.
4:30 p.m. — A tiki drink or two at Three Dots and a Dash, 435 N. Clark Street
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After dropping that pizza off in a fridge, it’s time to get back to business. Enter through the alley way behind Clark Street, and walk down the stairs to one of the best tiki bars in the country. Run by Lettuce Entertain You Enterprises, Chicago’s biggest restaurant empire, Three Dots is a tropical paradise in the middle of a bustling Midwestern metropolis. The rum collection is potent and the drinks are fabulous and fun. For a more intimate experience, book a time inside the Bamboo Room, the bar’s VIP space for high-end rum drinks.
- Every Important Chicago Cocktail Bar Mapped [ECHI]
7:30 p.m. — Dinner at Topolobampo, 445 N. Clark Street
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There may not be time to explore Chicago’s Mexican communities, but dinner at this one-Michelin-star restaurant is hardly a consolation prize. This is Rick Bayless’s premier restaurant as he serves up Mexican cuisine in a fine dining environment. Diners can choose from a five-course tasting menu or a seven-course option. Topolo is one of the most pioneering Mexican restaurants in the country and helped show Americans that their southern neighbor produces more than burritos and tacos.
- 25 Years In, Rick Bayless’ Topolobampo Is Still Changing Perceptions of Mexican Cuisine [ECHI]
10:30 p.m. — Drinks at Cindy’s, inside the CAA, 12 S. Michigan Avenue
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By this hour, it might be time for a walk. Head down Michigan Avenue and across Millennium Park to the Chicago Athletic Association hotel, a charming building that was recently rehabbed. Ignore the urge to grab a burger from Shake Shack on the first floor and head upstairs to experience one of the city’s best rooftop bars. Cindy’s offers potent potions and scenic lake views, as well as a full food menu if patrons are hungry.
- 20 Chicago Restaurants With Killer Views of the Windy City [ECHI]
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.
- The 20 Essential Dive Bars in Chicago [ECHI]
1:30 a.m. — Downtown Dogs
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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 Downtown Dogs 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.
- The 20 Essential Hot Dogs in Chicago [ECHI]
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