Go Christmas shopping, visit a winter festival and enjoy spectacular views from the tallest building in America, says Rebecca Pearson


The seventh annual "Chicaglo" season, a three-month festival of seasonal celebrations and family activities, reaches its climax in December. There are candlelit concerts and Christmas markets, and a particular highlight will be the Joffrey Ballet's presentation of The Nutcracker at the Auditorium Theatre , 50 East Congress Parkway (001 312 902 1500) from 5 December (tickets from $15-$90 (£10-£60). For more information and a programme of events, contact the tourist office on 001 877 244 2246; or visit www.877chicago.com/chicaglo.


December is a cheap time to go - search the internet for the best deals (www.deckchair.com is a good site) and you may well be able to find tickets for less than £300, including non-stop flights with British Airways. If you can travel before 15 December, Trailfinders (020-7628 7628) has flights from £229 with Air India. All international flights arrive at O'Hare airport, which is 17 miles north-west of downtown Chicago and vies with Atlanta for the title of busiest airport in the world.


From O'Hare airport, the "El" (short for elevated railway, as the CTA network is known) takes you anywhere in the city. At the airport station, invest $9 (£6.30) on a two-day unlimited-travel pass, and ask for the CTA map. Alternatively, a taxi will cost about $35 (£20). Once downtown, the main tourist offices are at Chicago Water Works , 163 East Pearson, open daily 7.30am-7pm; and in the Chicago Cultural Center, 77 East Randolph, open Mon-Fri 10am-6pm, Saturday 10am-5pm, and 11am-5pm on Sunday; 001 877 244 2246; www.choosechicago.com.


If it's spectacular you're after, try the Drake Hotel , 140 East Walton Place (001 312 787 2200; www.thedrakehotel.com), located just by Michigan Avenue, the shoppers' paradise. Expect to pay between $139 (£98) and $469 (£310) for the executive rooms. The Hotel Burnham , 1 West Washington (001 312 782 1111; www.burnhamhotel.com), has rooms from $169-$249 (£112-£166). The Days Inn Lincoln Park North , 644 West Diversey Parkway (001 773 525 7010; www.lpn daysinn.com) is in a great location close to Lincoln Park Zoo . Rates start from $111 (£74) for a double. The rates are for one person, and you pay $10 (£7) for each extra guest; children under 18free.


The Sears and Hancock Towers provide the best views. Although Sears is incredible (the tallest building in the US), don't overlook the Hancock . It's less touristy, but just as spectacular, with views spanning up to 80 miles. The Hancock Observatory at 875 North Michigan Avenue (001 312 751 3681), is open 9am to 11pm; $9.75 (£6.50). You should try out the Skywalk while you're there: although you're fenced-in, you can still feel what the air is like 1,000ft above the ground. At Sears, 233 South Wacker Drive (001 312 875 9696), you can visit the Skydeck , which is 1,353ft up. Admission is $9.95 (£6.60), and it's open May-September, 10am-10pm; October-April, 10am-8pm.


Start at the Art Institute (see Cultural Afternoon), then walk north up North Michigan Avenue, which will give you a chance to do some shopping. You can then head down a block or two west, and walk parallel with Michigan Avenue. It's not difficult to find your way back, and this way you'll avoid the crowds and find the smaller cafés. When you come to East Lake Shore Drive, there's a subway to get to Oak Street Beach . It's well worth a visit in the summer, but winter may be a little chilly...


Take advantage of the city's free "trolleys" which run between the Chicago Transit Authority (CTA), Metra and Amtrack stops, and drop you off at many popular tourist destinations, including the Navy Pier , the museum campus (incorporating the Field Museum, Shedd Aquarium and Plantetarium) and Michigan Avenue. They usually run every 20 to 30 minutes, and operate for longer at the weekends (10am-6pm), but it depends greatly on the time of year, so call the free number, 001 877 244 2246, for more information.


At Water Tower Place , 835 North Michigan Avenue (001 312 440 3165; www.shopwatertower.com) head to Foodlife, the food court. You'll find everything here from burgers and fries in a basket to fruit smoothies and luxury salads. Hectic, but fun.


The "Magnificent Mile", North Michigan Avenue, has far too many shops to list, but you could start at Marshall Field's flagship store, 111 North State Street (001 312 781 1000, open 9am-9pm Monday-Saturday, 11am-6pm Sunday), which boasts 10 floors of spending heaven. Water Tower Place is also worth a visit: it's the biggest mall on North Michigan Avenue with more than 100 shops, and comes complete with a welcoming water sculpture. Check out the giant candy-filled sign in the window of FAO Schweetz.


You won't get very far unless you carry ID proving you are 21 or over. However, if you can drink, a wonderfully lively place is Lalo's , 1960 North Clybourn (001 773 880 5256). See if you can fit one of their "medium" margarita glasses comfortably in one hand - a task made all the more tricky when you're applauding the live mariachi music.


If it's food with entertainment you're after, look no further than Ed Debevic's, , 640 North Wells Street (001 312 664 1707). There are good, hefty American burgers and giant salads, but it's the insults you go for. The waiters will shout at you and at each other, and then get up on the counter (it's a Fifties-style diner) and do Rose Royce's "Car Wash". Not for the shy and retiring, great for the children. For something completely different, try the Soundings Restaurant at the John G Shedd Aquarium , 1200 South Lake Shore Drive (001 312 939 2438). You can enjoy pasta, fish and grilled food with a spectacular view of Lake Michigan. A smaller, neighbourhood choice is Big Bowl , 6 East Cedar (001 312 640 8888). You won't be leaving hungry - the Asian food there is delicious.


The oldest public building in Chicago is Old St Patrick's church , 700 West Adams (001 312 648 1021; www.oldstpats.org), which was founded by Irish immigrants on Easter morning 1846. It's one of the few buildings to survive the Great Chicago Fire of 1871. There are regular services on a Sunday.


The best place for brunch has to be Toast , 2046 North Damen (001 773 772 5600), open 8am-4pm at the weekends, 7am-3pm during the week. A wonderful little restaurant worth travelling out for, Toast is just out of the way enough not to get too packed, but popular with the local residents. It has a light, airy feel, with a no-smoking policy, and it's very reasonably priced, with free refills on the thoroughly dreamy hot chocolate.


Follow in the footsteps of Ernest Hemingway and the architect Frank Lloyd Wright, and head to the picture-perfect suburb of Oak Park. The former was born here, and the latter lived in the area and designed 26 of its buildings. Frank Lloyd Wright's Home and Studio can be found at 951 West Chicago Avenue (001 708 848 1976; www.wrightplus.org); the official tour starts every 20 minutes from 11am to 3pm at weekends, and at 11am, 1pm and 3pm on weekdays and costs $9 (£6).


Buy a selection of postcards featuring Oak Park's gingerbread house-fronts and white picket fences from the museum shop at the Frank Lloyd Wright Home and Studio . Then wander back towards this peaceful suburb's main thoroughfare, Lake Street, window shopping at Fannie May's Chocolate Shop, before sinking into one of the vinyl booths, pen in hand, in the Cozy Corner Cafe, a Fifties-style diner complete with bouffant-haired waitresses.


The Art Institute , 111 South Michigan Avenue (001 312 443 3600; www.artic.edu) could easily take up most of your day with its collection of 300,000 works of art. There's a wide variety of objects from medieval armour to works by Andy Warhol here. It's open every day except Thanksgiving and Christmas Day. If you can go on a Tuesday it's free, while on other days you must give something (they recommend $10/£7).


The Field Museum , 1400 South Lake Shore Drive (001 312 922 9410; www.fmnh.org), boasts the world's largest and most complete T-rex - Sue - whose head is so heavy it has to be displayed separately from the body. It's open 9am-5pm every day except Christmas Day. On Mondays and Tuesdays, until 23 December, basic admission is free. Otherwise, it's $10 (£7) for an adult, and you might have to pay more on special exhibitions.