MidwestWeekends.com — Your Travel Guide to the Upper Midwest

Chicago

Halloween in Chicago

During scary season, this fun-loving city pulls out all the stops.

In high-spirited Chicago, Halloween is the most spirited weekend of the year.

We didn’t know that before we arrived one Halloween weekend, but then a few thousand Smurfs, zombies and cowboys bicycled past us on the monthly Critical Mass ride through Lincoln Park.

A pirate skull was perched on the turnips the next morning at the farmers market, and we saw oversized ghouls and witches waving from the windows of mansions. Downtown, orange gushers rose from the fountain in Daley Plaza.

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Chicago at Christmas

During the holidays, this glittering, festive town becomes the City of Broad Smiles.

Visiting Chicago during the holidays, I'm always bowled over by how merry everyone is.

Can it be . . . Chicago Nice? It's either that or pixie dust.

Chicago is an exciting place to be any time, but at Christmas, it pulls out the stops. The Magnificent Mile sparkles. Ice skaters do pirouettes in Millennium Park. There are free concerts everywhere.

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Cheap Chicago

Here are 10 tips to make a trip to the Windy City easy to afford.

Chicago is on a roll. Millennium Park is wildly popular, and it just keeps getting better, along with the rest of the city.

These days, tourists have to compete with hordes of conventioneers and suburbanites fleeing back to the city. Prices, of course, have gone up.

But Chicago is a populist town, and there's a lot to do for free. Here are 10 tips for making a trip affordable.

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10 great getaways from Chicago

Take a break to lounge on beaches, gawk at river canyons and go on brewery tours.

There's an endless number of fun things to do in Chicago, which is why tourists flock to it from around the world. To paraphrase the English wit Samuel Johnson, "When a man is tired of Chicago, he is tired of life.''

And yet, everyone needs to get out of town once in a while.

The traditional playground of Wisconsin lies to the north, and the beaches of  Michigan to the east. To the west, aim for destinations on rivers: the Fox, the Illinois, the Rock.

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Where to stay in Chicago

Want to visit the Windy City? So does everyone else. Here's how to find a place.

Chicago is a fun, fun place to be.

It's popular with conventioneers, families, students, girlfriend groups and couples on a romantic getaway. Everyone wants to join the festive mobs at Millennium Park, Navy Pier and, at Christmas, the Christkindlmarket in Daley Plaza.

There are nearly 40,000 hotel rooms downtown, which you'd think would be enough. Except in summer, when vacationers from around the world flood in. And whenever there's a big convention or event.

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Chicago as you like it

Beaches or museums, baseball or music? This fun-loving metropolis makes it hard to decide what to do first.

Chicago is like one big theme park. The thing is, you have to bring your own theme.

I have one every time I go there: Blues and bicycling. Museums and dim sum. Skyscrapers and food tours.

That's because the possibilities are endless. There's so much to do in Chicago that it's easy to bounce around like a kid in a candy store, overwhelmed by choices, as time runs out.

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Chicago with kids

For curious children, this inviting city overflows with treasures.

For parents, it's hard to predict what kids will like best about Chicago.

During spring break one year, my friend Rebecca and I took our children to Chicago, with an itinerary that alternated visits to museums with visits to zoos and parks.

Pitting high culture against popular culture, we knew what the biggest hits would be: the Ferris wheel at Navy Pier, Lincoln Park Zoo, the elevated train, deep-dish pizza, perhaps the Museum of Science and Industry.

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Chow-down in Chicago

In a city of neighborhoods, cooks from many countries stir the pot.

Chicago has come a long way since it was hog butcher to the world.

There was nothing very appetizing about early Chicago. The factories and slaughterhouses that made it grow also made it stink. Rotting carcasses made the Chicago River bubble; a glass of water came with a side of cholera.

But the city grew up. The immigrants who packed its meat, dug its waterways and built its railroads moved on and were replaced by new immigrants, who settled in places that became known as Little Italy, Andersonville, Polish Village, Ukrainian Village, Chinatown, Greek Town and Pilsen.

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Tales of the dead

At Chicago's famous Graceland Cemetery, the graves have a lot to say.

It isn't true that dead men tell no tales.

Actually, they can be quite chatty. At Graceland Cemetery in Chicago, their stories keep up to seven tour guides busy, especially during Halloween season.

Graceland's residents are a Who's Who of Chicago society: retailer Marshall Field, meat-packer Philip Armour, hotelier Potter Palmer, piano maker William Kimball.

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Spin City

On a bicycle, visitors can explore every inch of Chicago's lakefront.

Everything that’s worth doing, you can do along Chicago’s lakefront.

Seniors in Speedos climb out of Lake Michigan after swimming laps. Chess players hunch over boards in a 1957 pavilion that looks like the Jetsons’ carport. College girls fumble with kayaks in the shadow of yachts, and boys play beach volleyball.

Overhead, a biplane pulls a flapping beer banner through the sky.

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Paddling the Chicago River

After years of neglect, this urban waterway has become a place to play.

The Chicago River never has run clear.

Before settlers arrived, it was a lethargic prairie river that ran through a swamp the Potawatomi called Checaugou — for “swamp weed,’’ or “wild onion.’’

Then factories and slaughterhouses turned it into a sewer. At the confluence of the main branch with the north and south branches, Bubbly Creek was named for the methane gas that rose from decomposing carcasses on the river bottom.

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Pinching pennies in Chicago

It's easy to save money in this lively town . . . and to spend it, too.

If you love to visit Chicago, as we do, you have a compelling reason to look for discounts when you’re visiting — the more you save, the sooner you can return.

We traveled there over Memorial Day weekend, but we started looking for savings months in advance. First, I arranged a home exchange, so we didn’t have to pay for a hotel.

Then we signed up for local deal listings. Then we started looking for free things to do.

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Skyscraper city

For architecture fans, Chicago is the place to walk and gawk.

In Chicago, there’s great people-watching — but the building-watching is even better.

The city is best known for humongous buildings — the Willis (Sears) Tower, Hancock Center, Aon Building. But clustered around their knees are others that attract tourists from all over the world, buildings with so much flair it’s tempting to give them personalities.

There’s Helmut Jahn’s Thompson Center, the brassy showgirl with the heart of gold, and Ludwig Mies van der Rohe’s Federal Plaza, the geek with the thick black glasses.

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Into the belly of Chicago

A food tour points us toward pizza, candies, spice and everything nice.

Once, Chicago was a meat-and-potatoes town, the City of Broad Shoulders.

Chicagoans still brawl over who has the best deep-dish pizza and Chicago-style hot dogs, which come with no ketchup but so many condiments they're “dragged through the garden.’’

But these days locals are just as likely to seek out the best macarons and gelato, and on special occasions, they dine at Michelin-starred restaurants with avant-garde chefs who are more Jeff Koons than Betty Crocker.

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Globe-trotting in Chicago

From Chinatown to Andersonville, these colorful neighborhoods are a window into other worlds.

One Memorial Day weekend, my friend Grace and I went to tour "ethnic'' Chicago. But we'd only been there a few hours before we realized everything about Chicago is ethnic.

Chicago is a mosaic, a city of neighborhoods settled by waves of immigrants who arrived to dig its waterways, build its railroads and work in its slaughterhouses.

One of its first neighborhoods was Bridgeport, settled by Irish canal workers in the 1840s and the stronghold of Mayor Richard J. Daley and his son Richard M. Daley, the current mayor.

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