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Chicago’s 90-year-old Buckingham Fountain
Chicago’s Buckingham Fountain is one of the city’s icons in Grant Park.
Photo by Bilgin Sasmaz/Anadolu Agency/Getty Images

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

Make every second count

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

A pink covered old fashioned doughnut with sprinkles.
Doughnut Vault servers some of Chicago’s best.
Hogsalt [Official Photo]

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

Polar Vortex Weather System Brings Artic Temperatures Across Wide Swath Of U.S.
Get a view from the Hancock Center.
Photo by Scott Olson/Getty Images

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

A woman serving an Italian beef sandwich
Al’s Beef
Barry Brecheisen/Eater Chicago

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

A white space with tall ceilings and windows, light wood floors, and sleek monochromatic tables and chairs.
Pacific Standard Time
Barry Brecheisen/Eater Chicago

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

Chicago deep-dish pizza
Don’t wait in line for this.
Lou Malanti’s/Facebook

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

Three Dots new cocktails
Three Dots and a Dash has tiki drinks.
Lettuce Entertain You Enterprises [Official Photo]

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

A dimly lit dining room with shelves full of trinkets.
Topolobampo
Topolobampo [Official Photo]

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

A hand holding a popsicle with a few of Chicago’s Millennium Park.
Boozy popsicles and other treats could be enjoyed with a view at Cindy’s.
Cindy’s/AJ Trela

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

The outside of a dive bar.
Rossi’s
Google

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

The outside of a hot dog restaurant in Chicago with patio seating.
Downtown Dogs
Google

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]

Downtown Dogs

804 North Rush Street, , IL 60611 (312) 951-5141 Visit Website

Lou Malnati's Pizzeria

6649 Lincoln Avenue, , IL 60712 (847) 673-0800 Visit Website

Aster Hall

900 North Michigan Avenue, , IL 60611 (312) 995-0235 Visit Website

Al's Beef

1079 West Taylor Street, , IL 60607 (312) 226-4017 Visit Website

The Laurel Room

640 N LaSalle Drive, 8th Floor, Chicago, IL 60654 (312)736-1740 Visit Website

The Signature Lounge

John Hancock Center, Chicago, IL 60611 312-787-9596 Visit Website

Chicago Athletic Association

12 S Michigan Ave, Chicago, IL (312) 940-3552 Visit Website

Cindy's

12 South Michigan Avenue, , IL 60603 (312) 792-3502 Visit Website

Pacific Standard Time

141 West Erie Street, , IL 60654 (312) 736-1778 Visit Website

Topolobampo

445 N Clark St, Chicago, IL 60654 312-661-1434

The Doughnut Vault

111 N Canal St, Chicago, IL 60606

Rossi's Liquors

412 N State St, Chicago, IL 60654 (312) 644-5775 Visit Website

Three Dots and a Dash

435 North Clark Street, , IL 60654 (312) 610-4220 Visit Website
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