Chicago, Ten Years Running: A Winter City Break

Chicago has been voted Best Big City in the US by Condé Nast Traveler readers for 10 years in a row, the first city to hold the title that long, Choose Chicago announced on 6 October 2026. For Canadians, the more practical news came in September: Porter Airlines moved its Toronto Billy Bishop flights from Midway to O’Hare, three times daily. Chicago is a short flight from most of Ontario and Quebec, and its winter calendar, from holiday markets to museum shows, makes a strong case for a three- or four-night break between November and March.

Getting there

• Porter flies Billy Bishop–O’Hare three times a day on Dash 8-400s, a route it has flown to Chicago since 2008. O’Hare connects to its partner American Airlines, and Porter said a US preclearance facility was coming to Billy Bishop, which lets passengers clear US customs before departure.
• Air Canada and United fly Toronto Pearson to O’Hare, with service from other Canadian cities. Check current schedules from your airport.
• From O’Hare, the CTA Blue Line runs to the Loop.

What’s on this winter

Choose Chicago‘s fall 2026 to winter 2027 calendar has more than enough for a long weekend:

• Christkindlmarket Chicago, marking its 30th anniversary, runs at Daley Plaza from 20 November to 24 December 2026, and in Wrigleyville through 31 December.
• Magnificent Mile Lights Festival, its 35th edition, on 21 November.
• Holidays @ Skydeck in the Willis Tower, 13 November 2026 to 4 January 2027.
• The Joffrey Ballet‘s The Nutcracker, set at the 1893 World’s Columbian Exposition, 4 to 27 December.
• One of a Kind Holiday Show at THE MART, 3 to 6 December, with 600-plus makers.
• Chicago Thanksgiving Parade on State Street, 26 November. US Thanksgiving weekend is busy; plan around it.

Museums and shows

• Field Museum: the North American debut of the Pokémon Fossil Museum runs to 11 April 2027, a win for families.
• National Museum of Mexican Art in Pilsen: 40 years of its Día de Muertos exhibition, 25 September to 29 November 2026.
• Intuit Art Museum: a Henry Darger paper-craft exhibition to 31 January 2027.
• Chicago Shakespeare Theater on Navy Pier begins its 40th season this fall with The Winter’s Tale and A Midsummer Night’s Dream in repertory.
• Greektown’s 40 free public artworks along South Halsted Street, part of America’s 250th, run to May 2027.
• Brookfield Zoo: Holiday Magic lights, 20 November to 3 January.

Where to eat and drink

New since the summer, according to Choose Chicago:

• Black Briar, an American tavern in Fulton Market from chef Jimmy Papadopoulos, opened 26 September.
• Berenjak, a Persian restaurant, opened its first Chicago location at Soho House Chicago.
• Tarra & Sura in River North: Thai restaurant upstairs, cocktail lounge below.
• The Carlyle Club, an all-day American concept at 316 N. Clark St.
• For a splurge, NoMI at Park Hyatt Chicago runs special events through its Heritage Series.

To mark the 10th Best Big City win, Goose Island is pouring a “Perfect 10” beer at its brewpubs and Eli’s Cheesecake has a Perfect 10 cheesecake flight through the holidays.

The click-worthy fact

Chicago had 56.8 million visitors in 2025 and a record $21.5 billion in visitor spending, Choose Chicago says, with records for leisure hotel demand, average daily rate and RevPAR. The city’s hotels did well without the Canadians who stayed home. Its tourism board would like them back.

Plan it

• When: mid-November to early January for markets and lights; January to March for the best hotel value and museum days. Dress for cold and lake wind.
• Length: three or four nights.
• Costs: at about 70 US cents to the loonie in early October 2026, a $300 hotel night is roughly C$428. Weekends around US Thanksgiving and the Christkindlmarket opening price highest.
• Getting around: walk the Loop and the Riverwalk, and use the CTA trains; skip the car.

Sources

• Choose Chicago, Best Big City for 10th year, 6 Oct 2026
• Choose Chicago, What's New Fall 2026–Winter 2027, 10 Sept 2026
• Porter Airlines via Business Wire, Feb 2026
• Pound Sterling Live, CAD/USD 2026