Head straight from the airport to the James Hotel to check in, and then head down to David Burke’s Primehouse, the hotel restaurant, for dinner. Chicago is known for its steakhouses, and this one doesn’t disappoint. Savor one of the dry-aged prime cuts (aged on the premises in their Himalayan salt-tiled room) along with a specialty cocktail.
After steak, walk a few blocks north to the Hancock Tower. Bypass the observation deck’s long lines (and steep price) by taking an elevator to the 96th floor’s Signature Lounge. Take in one of the best views in the city here, all for the cost of a drink. After paying the tab, grab a cab to the Green Mill, one of the city’s most iconic jazz clubs, to hear some of the best local and international acts around.
The James Chicago, 55 E Ontario St, Chicago, IL, USA, +1 312 337 1000
The Signature Lounge, 875 N Michigan Ave, Chicago, IL, USA, +1 312 787 9596
Green Mill, 4802 N Broadway Ave, Chicago, IL, USA, +1 773 878 5552
Shake off a late night (and probable hangover) with breakfast at Beatrix. Order some coffee – then wrestle with what to order (we love the braised pot roast and egg sandwich). They also have a menu of fresh-squeezed juices, which are ideal for helping to undo some of the previous night’s damage. After breakfast, spend the morning strolling Michigan Avenue (also called the “Mag Mile”), a mile-long stretch of high-end shopping mixed with notable Chicago architecture (like the Tribune Tower, Wrigley Building, and Chicago Water Tower).
Beatrix, 519 N Clark St, Chicago, IL, USA, +1 312 284 1377
If the weather is nice, a boat tour is a must. Wendella, located at the northwest corner where Michigan Avenue meets the river, sells tickets for both river and lake cruises. For the best of both worlds, hop on a 90-minute combination tour that travels down one branch of the Chicago River before heading out onto Lake Michigan. Definitely bring a camera (and sunscreen – the sun can be brutal out on the water). After getting back on land, head to Portillo’s, a Chicago institution that serves up some of the best Chicago-style hot dogs in town, as well as another lesser-known iconic Chicago dish, Italian Beef.
Wendella Boat Tours, 400 N Michigan Ave, Chicago, IL, USA, +1 312 337 1446
Portillo’s, 100 W Ontario St, Chicago, IL, USA, +1 312 587 8910
Wind down the whirlwind tour with a stop in hip Wicker Park. Stroll the streets checking out the bookstores and vintage boutiques before heading to Big Star for some of the best tacos in town. Grab a seat on the always-busy patio and order up some tacos al pastor before heading back to the airport.
Big Star, 1531 N Damen Ave, Chicago, IL, USA, +1 773 235 4039