Why go now?
As the snow starts to fall like icing sugar on the USA’s third-largest city (after New York and Los Angeles) this Thanksgiving weekend, festive cheer is palpable. With temperatures hovering around freezing, there’s plenty to take your mind off the cold, including a vibrant cultural and culinary scene. As Mark Twain said, “It is hopeless for the occasional visitor to try to keep up with Chicago. She is always a novelty.”
American Airlines (0844 499 7300; americanairlines.co.uk) flies from Heathrow and Manchester; its partner, BA (0844 493 0787; ba.com), flies from Heathrow, as does United Airlines (0845 607 6760; united.com).
Chicago O’Hare airport is 17 miles north-west of the city centre. The cheapest and most reliable way to reach downtown is on the Blue Line of the “L”, as Chicago’s rail system is known (derived from “elevated” – originally all the lines were above ground). It takes 45 minutes to reach downtown, stopping at Washington Station (1). Buy a three-day ($14/£9) or seven-day ($23/£14) pass, or a stored-value card, in advance from the ticket machines ( transitchicago.com). Standard one-way fare: $2.25 (£1.40). A taxi costs about $50 (£31).
Get your bearings
Chicago stretches along the south-west shoreline of Lake Michigan. Its downtown district is bordered to the west by the Chicago River. The tourist centre (2) (001 312 742 0808; choosechicago.com; 9.30-6pm daily, 10am-5pm Sundays) is inside the Water Works pumping station on East Pearson Street.
The skyscraper was born in Chicago. The city’s two most iconic buildings – the Willis Tower (3) (formerly Sears) and the John Hancock Center (4) – stand like giant slate bookends, framing the dramatic skyline.
Check in Inspired by 17th-century France, the Sax Hotel (5) (001 877 569 3742; hotelsaxchicago.com) at 333 North Dearborn Street is bold and decadent. Doubles start at $208 (£130), room only.
The James Hotel (6) (001 312 337 1000; jameshotels.com) at 55 East Ontario Street offers comfort in a contemporary setting. The neutral tones give the rooms a calming quality while the modern furnishings, such as the Saarinen replica tables, add a dash of style. Doubles from $197 (£123), room only.
Overlooking Grant Park and Lake Michigan, the Essex Inn (7) (001 312 939 2800; essexinn.com) at 800 South Michigan Avenue is a good option for those on a budget.
Take a view
At 1,450ft tall, the Willis Tower (3) (001 312 875 9447; theskydeck.com) at 233 South Wacker Drive is the tallest building in the western hemisphere. The observatory on the 103rd floor offers a dramatic panorama; 10am-8pm daily; admission $17.50 (£11).
Take a hike
… along State Street, which runs straight through the heart of the Loop, the historic and rugged downtown district. Start at the corner of West Jackson Boulevard and walk north – you’ll pass Macy’s (8) and the landmark 1921 Chicago Theatre (9). Cross the Chicago River on the DuSable Bridge (10), noting the diverse architecture of the riverside buildings, and finish outside the neo-Gothic Tribune Tower (11). A look at the exterior walls reveals fragments from far and wide: the Berlin Wall, Taj Mahal, Pyramids and Great Wall brought back by globetrotting reporters.
Lunch on the run
Home to the original deep-dish pizza, Uno (12) at 29 East Ohio Street (001 312 321 1000; unos.com) has become an institution since serving its first slice in 1943. Order the signature Numero Uno, oozing with melted cheese and chunks of sausage and pepperoni. From $10 (£6).
The Magnificent Mile ( themagnificentmile.com) is a tree-lined stretch of North Michigan Avenue, running north from the Tribune Tower (11). Luxury retailers – Burberry, Gucci, Louis Vuitton – compete. The shopping elsewhere is no less magnificent. Armitage Avenue (13) ( armitageshopping.com) in the Lincoln Park suburb is lined with independent stores and charming Victorian houses. Opening hours are typically 11am-6pm daily.
Over 105 years, the Green Mill Jazz Club (14) (001 773 878 5552; greenmilljazz.com) at 4802 North Broadway has attracted everyone from Charlie Chaplin to Al Capone. Expect strong drinks, world-class music and a packed dance floor. Order a shot of Malort ($5/£3), Chicago’s own gold-coloured spirit made from an old Swedish recipe using wormwood plants.
Dining with the locals
Under chef Carrie Nahabedian, Naha (15) (001 312 321 6242; naha-chicago.com), at 500 North Clark Street, won a Michelin star. Try the Icelandic Arctic char in an apple and celery broth ($34/£21).
Southern-inspired dishes await at the Carriage House (16) (001 773 384 9700; carriagehousechicago.com) at 1700 West Division. Cider-steamed clams are $16 (£10).
Sunday morning: go to church
Old St Patrick’s Church (17) (001 312 648 1021; oldstpats.org) at 700 West Adams Street may be Chicago’s most celebrated place of worship, but St Hedwig’s (18) (001 773 486 1660; sthed wigbucktown.org) at 2226 North Hoyne Street is an undiscovered gem. Built at the turn of the 20th century to serve the city’s growing Polish community, it’s the oldest church in Bucktown, a bohemian neighbourhood to the north that warrants exploration. (A cab will cost $15/£9.) Within its limestone walls are Bavarian stained windows. Sunday mass is at 8am and 11am.
Out to brunch
At the redbrick Bite Café (19) (001 773 395 2483; bitecafechicago.com) at 1039 North Western Avenue, choose from home-made granola with yoghurt, tacos with scrambled eggs or a “poached egg and bacon hangover salad”. From $9 (£5).
Walk in the park
Millennium Park (001 312 742 5222; millenniumpark.org; 6am-11pm daily) was once forgotten wasteland. Today, explore the colourful Lurie Garden (20), check out Anish Kapoor’s metallic and bean-shaped installation Cloud Gate (21), inspired by liquid mercury, and skate on the McCormick Tribune Ice Rink (22) ($10/£6; open until March). In warmer months, concerts are staged under the lattice arches of Frank Gehry’s Jay Pritzker Pavilion (23).
Discover the secrets of the city at the Chicago History Museum (24) at 1601 North Clark Street (001 312 642 4600; chicagohs.org; open noon-5pm Sunday, 9.30am-4.40pm other days; $14/£9). Alternatively, marvel at Monets and Renoirs at the Art Institute of Chicago (25) at 111 South Michigan Avenue (001 312 443 3600; artic.edu; 10.30am-5pm daily, to 8pm Thursdays; $18/£11).
The icing on cake
Discover a wealth of outdoor art, from Picasso’s sculpture (26) outside 50 West Washington Street to Chagall’s vibrant mosaic at Exelon Plaza (27) on Monroe Street.