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Chicago Vacations

Writer Nelson Algren was right on the money when he wrote that loving Chicago was 'like loving a woman with a broken nose: you may well find lovelier lovelies, but never a lovely so real'. There's just something about this cloud-scraping city that bewitches.

The Windy City may get slapped by brutal, six-month winters but, come May, everyone dashes for the outdoor festivals, ballparks, lakefront beaches and beer gardens - ahh, nowhere tops Chicago. Literally: the Willis Tower is here, the USA's tallest building.

Region: USA

Featured Chicago Travel Deal

The Westin Michigan Avenue Chicago

Traditional King, Exclusive $50 Off per booking, Stays of 5 nights or longer receive exclusive $100 Off per booking, Kids 17 & younger stay FREE

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Featured Chicago Hotel

The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

Our 4-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway.
Magnificent Mile, Chicago, IL

This elegant hotel on the Magnificent Mile offers easy access to upscale shopping at Water Tower Place.

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What To Do

Have your own urban adventure and canoe the Chicago River, retracing the route of French trapper Louis Jolliet. Besides urban sprawl, you're likely to see deer, red fox, beaver and birds. Chicago's push for more parks and houses along the river is providing a more aesthetically pleasing paddle.

What To See

The lake is an ocean, the buildings scrape the sky.

Loaf your way around the Loop, Chicago's 'inner circle', and imbibe its busy daytime hum and after-hours hipness. Put your head in the clouds at Sears Tower or treasure the impressionist collection at the Art Institute of Chicago, one of the world's premier museums.

Willis Tower
Yes, you're at the right place. Willis Tower was the Sears Tower until mid-2009, when insurance broker Willis Group Holdings bought the naming rights. No matter what you call it, its 103rd-floor Skydeck puts visitors way up in the clouds. There's a factoid-filled film to watch, and then the ear-popping, 70-second ride to the top. Step onto the glass-floored Ledge for a feeling of mid-air suspension and knee-buckling view straight down. For those who prefer a drink with their vista, the Gold Coast's John Hancock Center is a better choice.

Goose Island Brewery
Goose Island’s popular beers are served in bars and restaurants around Chicago, but it tastes best here at the source. The pub pours the flagship Honker’s Ale and 14 or so other potent brews. Fine grub complements the brews; special kudos to the Stilton burger and chips.

Buckingham Fountain
This is one of the world’s largest squirters, with a 1.5 million gallon capacity and a 15-story-high spray. Wealthy widow Kate Sturges Buckingham gave the magnificent structure to the city in 1927 in memory of her brother, Clarence. She also wisely left an endowment to maintain and operate it. The central fountain symbolizes Lake Michigan, with the four water-spouting sea creatures representing the surrounding states. The fountain lets loose on the hour. At night (8pm and thereafter) multicolored lights and music accompany the show.

Lincoln Park Conservatory
‘It’s like a free trip around the world,’ one visitor said after walking through the conservatory’s 3 acres of desert palms, jungle ferns and tropical orchids. We couldn’t agree more, especially in winter, when the glass-bedecked hothouse remains a soothing 75°F escape from the icy winds raging outside. Just south, the 1887 statue Storks at Play has enchanted generations of Chicagoans. Real birds fill the landscape immediately northeast, at the corner of Fullerton Pkwy and Cannon Dr, around the Alfred Caldwell Lily Pool. The Prairie-style garden, whose stonework resembles the stratified canyons of the Wisconsin Dells, is an important stopover for migrating species. It’s a magical, dragonfly-dappled refuge, open from late April through November.

Route 66 Sign
Attention Route 66 buffs: the Mother Road’s starting point is here. Look for the sign that marks the spot on Adams St’s north side as you head west toward Wabash Ave.

Boystown
What the Castro is to San Francisco, Boystown is to the Windy City. The mecca of queer Chicago (especially for men), the streets of Boystown are full of rainbow flags and packed with bars, shops and restaurants catering to the residents of the gay neighborhood.

Millennium Park
Rising boldly by the lakefront, Millennium Park is a treasure trove of free and arty sights. Frank Gehry's 120ft-high swooping silver band shell anchors what is, in essence, an outdoor modern design gallery. It includes Jaume Plensa's 50ft-high Crown Fountain, which projects video images of locals spitting water, gargoyle style; the Gehry-designed BP Bridge that spans Columbus Dr and offers great skyline views; and the McCormick Tribune Ice Rink that fills with skaters in winter (and alfresco diners in summer). The newest installment is the Nichols Bridgeway that arches from the park up to the Art Institute's 3rd-floor contemporary sculpture garden (free to view). However, the thing that has become the park's biggest draw is 'the Bean' – officially titled Cloud Gate – Anish Kapoor's ridiculously smooth, 110-ton, silver-drop sculpture. Locals and visitors alike find it hard to resist such playful art, as you'll see from all the folks splashing around in Crown Fountain and touching the sculpture. In summer, Millennium's acoustically awesome band shell – Pritzker Pavilion – hosts free concerts at lunchtime and at 6:30pm. For the latter, bring a picnic and bottle of wine and tune in to new music on Mondays, jazz and world music on Thursdays, and classical music on most other days.

Argyle Street
Also known as ‘Little Saigon.’ Many residents came here as refugees from the Vietnam War and subsequently filled the storefronts with pho-serving lunch spots, bubble-tea-pouring bakeries and shops with exotic goods from the homeland.

Obama's House
Hefty security means you can’t get close to Obama’s house, but you can stand across the street on Hyde Park Blvd and try to glimpse over the barricades at the redbrick Georgian-style manor.

Shopping

Barbara’s Bookstore
For serious fiction, you can’t touch this locally owned chain. Staff members have read what they sell, and touring authors regularly give readings.

Threadless
Those seeking that perfect ironic, eccentric, limited-edition T-shirt will find it at Threadless. The company runs an ongoing T-shirt design competition on its website in which designers submit ideas and consumers cast votes (750,000 weekly). The company then releases the seven winning styles in limited quantities of 1500, and they’re only available for two weeks.

Maxwell Street Market
Every Sunday morning hundreds of vendors set up stalls that sell everything from Jesus statues to 10 packs of tube socks to power tools. Don’t let the name mislead you: the market is not actually on Maxwell St, though it was for decades until gentrification forced it onward. It has become a hot spot for foodies craving homemade churros, tamales, gorditas and other Mexican noshes, and for folks seeking cheap clothing, electronics and junk galore.

Nightlife

Second City
A Chicago must-see, this club is best symbolized by John Belushi, who emerged from the suburbs in 1970 and earned a place in the Second City improv troupe with his creative, manic, no-holds-barred style. Belushi soon moved to the main stage, and then to Saturday Night Live, and then on to fame and fortune. A who’s-who of funny people have followed a similar path: Billy Murray, Steve Carell, Amy Poehler and many more. Second City’s shows are sharp and biting commentaries on life, politics, love and anything else that falls in the crosshairs of the comedians’ rapid-fire, hard-hitting wit.

Redmoon Theater
The interaction of humans and puppets is key to the magical, haunting adaptations of classic works like Moby Dick and new commissions like The Princess Club, a fairly twisted look at children’s fairy tales. The innovative nonprofit troupe, headed up by performance artists Blair Thomas and Jim Lasko, never fails to mesmerize.

Aviary
Grant Achatz's bar beside Next is more in spirit (pun!) with his other restaurant, Alinea. The lounge shakes and stirs one-of-a-kind drinks such as Buttered Popcorn, which tastes as advertised. The selection changes frequently, as do the 19 different types of ice. Drinks cost around $16 each.

Events

Blues and jazz musicians have been flocking to Chicago since 1915, so it's no surprise that the city knows how to celebrate its musical heritage with style. The Chicago Blues Festival is a highly regarded three-day festival held in Grant Park on the first weekend in June. Soon after, Grant Park hosts the weekend-long Chicago Gospel Festival and, on Labor Day weekend, the Chicago Jazz Festival.

Taste of Chicago is an enormous festival that closes Grant Park for 10 days leading up to Independence Day in July. Over 100 local eateries serve some of the greasiest food you've ever tried to rub off your fingers. Live music on several stages drowns out the rumble of the belches from the 3.5 million people who attend. The German-American Festival is an enjoyable Oktoberfest-type event held in the heart of an old German neighbourhood at Lincoln Square during the third weekend in September.

In May, artsy types get along to Art Chicago. This massive mid-month festival on Navy Pier is a Very Big Deal in Chicago's art world. Over 3000 artists are featured, and city-wide events are held at museums and galleries. Also features the Stray Show, a separate event for up-and-coming artists.

Food and Drink

Charleston
The resident cats curl up on your lap at this laid-back favorite of Bucktown locals. When the occasional folk and bluegrass acts set up in the middle of the narrow room, it gets crowded, but it’s definitely worth it.

Alinea
Helmed by superstar chef and James Beard Award–winner Grant Achatz, the small room at Alinea is widely regarded as Chicago’s most exciting dinner spot, where giddy, awestruck culinary cognoscenti document each course with a digital photo before eating it. The options are limited to a 12-course ‘tasting’ and a 20-plus-course ‘tour’, bringing an artistic carnival of strange pairings served in steel and glass contraptions. The once-in-a-lifetime meal can take upwards of four hours, and you can add a note-perfect wine pairing for an additional fee. Reserve well in advance.

Chicago Chop House
In the proud tradition of Chicago chops, this comfortable, upscale, independently owned steak house is king. Look forward to perfectly cured meats hand cut on-site, and an atmosphere befitting the city’s famous politicos and mob bosses – many of whom look down from framed portraits lining the walls.

Crisp
Music pours from the stereo and cheap, delicious Korean fusions arrive from the kitchen at this cheerful cafe. The ‘Bad Boy Buddha’ bowl, a variation on bibimbap (mixed vegetables with rice), is one of the best $8 lunches in town. On second thought, maybe that award goes to Crisp’s burrito, filled with perfectly fried chicken in a savory soy-ginger sauce.

Big Star Taqueria
Once a filling station, now a taco-serving honky-tonk bar helmed by a big-name Chicago chef (Paul Kahan). So goes gentrification in Wicker Park. The place gets packed, but damn, those tacos are worth the wait – pork belly in tomato–guajillo chili sauce and lamb shoulder with queso fresco (creamy white cheese) accompany the specialty whiskey list. If the table- studded patio is too crowded, order from the walk-up window. Cash only.

Next
Grant Achatz's West Loop restaurant is the hottest ticket in town. And we mean it literally – you need a ticket to dine at Next, which operates like a time machine. It started by serving an eight-course French meal from 1906 Paris, but every three months the whole thing changes: new era, new menu, new decor. Sign up for tickets at the website as early as possible.