United States
Chicago
We visited in February

In February the case for a walking tour of Chicago is best made indoors. Ours was of the buildings of Mies van der Rohe, who came to the city in the late 1930s to head the architecture school at what became the Illinois Institute of Technology, and stayed. The case against was waiting outside: daytime highs in the 30s Fahrenheit, and a wind off Lake Michigan that bites hardest across the open ground of Millennium Park. The idea was received coolly, which suited the forecast, and agreed to all the same.
For one of us it became a real highlight of the trip, and the guide was the reason: the buildings were known so thoroughly that standing still at that temperature seemed a fair price. The Federal Center at 219 South Dearborn Street is three of Mies's buildings around a plaza, their steel mullions painted flat black and the glass between them tinted bronze. In the plaza stands Alexander Calder's Flamingo, 53 feet of red steel and the warmest-looking thing in the Loop in February.
Go in May or October if the walking is the point; October is usually the driest month of the year. Summer is hot and at its most expensive. Winter has rooms at their cheapest and museums at their emptiest, which is a case, again, best made indoors.
Stay in the Loop. We were across the street from Millennium Park, in a hotel that was a treat: the design stands out, and the bill did not. Cloud Gate is in the park and the Art Institute a few minutes' walk south along Michigan Avenue, so in winter it is never far from one warm door to the next. Near North, over the river, has the Magnificent Mile's shops and River North's galleries and bars instead.
Dinner is a short cab ride west, in the West Loop, where the old meatpacking warehouses around Fulton Market have become the city's busiest restaurant row. Girl & the Goat is on Randolph Street there, shared plates out of a 30-foot open kitchen, and we ate very well at it and at a couple of other places besides. The deep-dish pizza came from a takeaway that works like a slice shop, and the hot dogs from the most famous place in town for them; neither name survived the trip home. The recipe is easier to keep: all-beef, a poppy seed bun, neon-green relish and a dill pickle spear among the toppings. Ketchup is not one of them, and a good many vendors will not so much as offer it.
- Best months
- April to May and September to October
- Avoid
- January and February, when daytime highs average only in the 30s°F and the city gets most of its roughly 37 inches of snow a year.
- Nearest airport
- Chicago O'Hare (ORD)
- Transfer
- about 45 minutes
Neighbourhoods
- Lincoln Park and the North Side
Where to stay
5 hotels
5 hotels
Grown-upChicago Athletic Association
£Chicago, United States
An 1893 gentlemen's club on Michigan Avenue, converted in 2015 with its staircases and billiard rooms intact, and a rooftop bar facing Millennium Park.
Grown-up & familyPendry Chicago
££Chicago, United States
Black and white marble stripes in the lobby, and gold leaf on the crown of a 1929 Art Deco tower that was drawn, the story goes, as a bottle of champagne.
Grown-upSoho House Chicago
££Chicago, United States
Giant chandeliers hang against the bare brick of a 1907 Fulton Market leather works, and the bigger bedrooms are done in velvet and veneer.
Grown-upThe Hoxton, Chicago
££Chicago, United States
Stephanie Izard's ceviche and a pool share a roof above the old meatpacking streets of Fulton Market.
Grown-up & familyThe Robey
££Chicago, United States
A wedge of 1929 Art Deco at Wicker Park's six-way junction, built as offices for doctors and lawyers, with cocktails and the skyline on the 13th floor.
Where to eat
6 restaurants

El Che Bar
We ate there
West Loop · Argentine steakhouse
Wood-fired asado-style steaks and oysters off a flame-lit open grill, including a 22oz bone-in ribeye.
Reviewed in The Infatuation and the Michelin Guide

Girl & the Goat
£££ · We ate there
West Loop · global fusion
Stephanie Izard's shareable small plates in the West Loop, anchored by green beans unchanged on the menu since 2010.
Reviewed in The Infatuation and the Michelin Guide

Frontera Grill
££ · Recommended
Near North · Mexican
Rick Bayless's regional Mexican cooking since 1987, with deeply spiced moles, hand-pressed tortillas and table-shaken margaritas.
Reviewed in The Infatuation and the Michelin Guide

Kasama
££££ · Recommended
Filipino
Filipino tasting menus with two Michelin stars at night, and a bakery for truffle croissants by day.
Reviewed in The Infatuation and the Michelin Guide

Monteverde
£££ · Recommended
West Loop · Italian
Handmade pasta rolled at the open pastificio, from cacio whey pepe to a pork neck ragu alla Napoletana.
Reviewed in The Infatuation and the Michelin Guide

Oriole
££££ · Recommended
West Loop · Contemporary American
A thirteen-course tasting menu blending French and Japanese technique, entered through a converted freight elevator in Fulton Market.
Reviewed in The Infatuation and the Michelin Guide
