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Chicago Guide

Travellers' Choice award winner
Travellers' Choice™ 2014 Winner Destinations
  • Holiday Ideas (6)
  • Walking tours (18)
  • Before You Go
  • Travellers' Picks (185)

Best of Chicago

3 days in Chicago
3 days in Chicago

The Field Museum and Art Institute are top Chicago museums that can't be missed. After a day of shopping on the Magnificent Mile, catch a show at the Chicago Theatre.

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Family-friendly Chicago

Chicago for young kids
Chicago for young kids

Chicago has several museums geared toward kids, including the Museum of Science and Industry, the Chicago Children's Museum and the Peggy Notebaert Nature Museum. Kids will have so much fun they won't even realize they're learning!

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Chicago on a budget

Chicago For free
Chicago For free

Parks, zoos, conservatories and museums can all be enjoyed for free for those in Chicago on a budget. You can even take a free Chicago Greeter tour to explore a new neighbourhood!

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Insiders' Chicago

Chicago off the beaten path
Chicago off the beaten path

Take the L (that's Chicagoese for elevated train) to explore Chicago neighbourhoods like Chinatown and Wicker Park. Or visit a museum that many locals haven't even been to like the National Museum of Mexican Art or the Jane Addams Hull-House Museum.

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Chicago's Incredible Nightlife
Chicago's Incredible Nightlife

Chicago may just have the best all-around nightlife scene in the country. From a legendary improv theatre to amazing jazz joints to the world's most avant-garde cocktail lounge, check out Chicago's top nightlife destinations.

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Getaways from Chicago

Daytrips from Chicago
Daytrips from Chicago

Whether it's a beautiful suburb like Oak Park or Naperville, or a weekend escape to Lake Geneva, Wisconsin, Chicago has plenty to offer outside of the city itself.

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EveryTrail
Best of Chicago
Best of Chicago

Chicago feeds on extremes, and on its own uncanny knack for reinvention—a trait that likely began with the Great Fire of 1871, which devoured one-third of the city. It’s hard to think of another...

Rated 5 out of 5 by EveryTrail members
Chicago Tour: Bucktown and Wicker Park
Chicago Tour: Bucktown and Wicker Park

Bucktown meets Wicker Park just north of the bustling intersection of Milwaukee, Damen, and North Avenues, yielding a hodgepodge of upscale boutiques and vintage shops; mom-and-pop eateries and...

Rated 5 out of 5 by EveryTrail members
Chicago Tour: River North
Chicago Tour: River North

Partly bordered by the Chicago River, River North is home to art galleries, boutiques, restaurants, bars, and clubs. There’s something for everyone here, and for every budget. Eat lunch at a Chicago...

Rated 5 out of 5 by EveryTrail members
A Celebration of Mexican Culture in Pilsen
A Celebration of Mexican Culture in Pilsen

Chicago’s Pilsen neighborhood has seen plenty of immigrant groups come and go. The first to arrive were Irish and Germans, followed by Poles and Czechs, who named the area after their hometown...

Rated 4 out of 5 by EveryTrail members
A Nature Lover's Guide to Lincoln Park
A Nature Lover's Guide to Lincoln Park

Lincoln Park is the neighborhood surrounding the northernmost stretch of a parcel of public land, also called Lincoln Park, that is part forest, part lakefront, part wetland and part cultivated garden...

Rated 5 out of 5 by EveryTrail members
Gangster Driving Tour
Gangster Driving Tour

Michael Jordan. Mayor Daley. Al Capone. No matter where you go around the world, these are three Chicagoans people most want to know about. Al Capone was just a cocky tough kid from Brooklyn when...

Chicago Tour: Lincoln Park
Chicago Tour: Lincoln Park

Much of Lincoln Park was destroyed in the Great Chicago Fire of 1871, and the neighborhood rebuilt its residences with stone and brick. Now Lincoln Park is an exhibition of Victorian architecture....

Rated 5 out of 5 by EveryTrail members
Eating and Entertainment at Navy Pier
Eating and Entertainment at Navy Pier

Navy Pier has been through a lot since it opened in 1916 as an entertainment venue and Great Lakes cargo facility. During its life, the pier has housed soldiers, the Red Cross and civil defense units,...

Culture and the Cubs in Wrigleyville
Culture and the Cubs in Wrigleyville

Wrigleyville is the neighborhood around the "friendly confines" of Wrigley Field, home of the hapless Chicago Cubs. This legendary National League team has fans around the world despite not having...

Millennium Park with Kids
Millennium Park with Kids

The 21st century dawned four years late in Chicago. But when Millennium Park finally opened in 2004, residents quickly forgave the late arrival and cost overruns. The park is a monument to the City of...

Rated 5 out of 5 by EveryTrail members
Chicago Tour: Andersonville
Chicago Tour: Andersonville

A historically Swedish community, Andersonville today is a collage of cultures. Walk along Clark between Foster and Bryn Mawr, and you’ll come across hookahs, sushi, handmade soaps, pastrami...

Rated 5 out of 5 by EveryTrail members
Chicago Tour: West Loop
Chicago Tour: West Loop

Originally a warehouse district, West Loop is quickly becoming home to upscale residences, restaurants, and galleries. Many businesses occupy former warehouses, taking care to display the old brick...

Rated 5 out of 5 by EveryTrail members
Chicago Tour: The Loop
Chicago Tour: The Loop

The downtown track of Chicago’s ‘L’ train encompasses most of the neighborhood known as the Loop. Home to some of Chicago’s most prominent institutions and landmarks, the Loop offers one great...

Rated 5 out of 5 by EveryTrail members
Chicago Tour: Gold Coast
Chicago Tour: Gold Coast

Prominent Chicago businessman Potter Palmer built Palmer Mansion on Lake Shore after the Great Chicago Fire of 1871, establishing the opulent standard of the Gold Coast neighborhood. Today, the Gold...

Rated 5 out of 5 by EveryTrail members
Shopping the Magnificant Mile and Oak Street
Shopping the Magnificant Mile and Oak Street

Start at the corner of Chicago and Michigan avenues so you can snap a few photos in front of the historic Water Tower. Built in 1869, it's the second oldest in the United States. The Water Tower...

Walking Tour of Public Outdoor Art in the Loop
Walking Tour of Public Outdoor Art in the Loop

Chicago is famous for its iconic architecture, but it's quickly gaining a worldwide reputation for its iconic public art as well.

The work of famous artists including Pablo Picasso, Jean Miro and...

The Museum Campus and Lakefront
The Museum Campus and Lakefront

Chicago's Museum Campus was created in 1998 when the northbound lanes of Lake Shore Drive were re-routed slightly west to make it possible to link three of Chicago's world-class museums—the Field...

President Obama's Neighborhood
President Obama's Neighborhood

Chicago is the adopted hometown of President Barack Obama, who gained his political bona fides, started his family and launched himself into the White House from the South Side. There are a smattering...

Rated 5 out of 5 by EveryTrail members

Perfect Day

white sox weekend (chijoe, 9 Mar 2007)
4.5 of 5 stars 1 Vote
3.5 of 5 stars 3 Votes
Enjoy Chicago (snowbiz100, 1 May 2006)
3.0 of 5 stars 6 Votes

Perfect Weekend

Chicago With A Pre-Teen (cecomp76, 9 Jan 2007)
4.5 of 5 stars 12 Votes
Wrigleyville in a Weekend (girlchicago, 24 May 2006)
4.5 of 5 stars 30 Votes
Chicago with a marathonist (Oscar A, 22 Oct 2007)
4.5 of 5 stars 1 Vote

Best Of

Top 10 Kid-Friendly Chicago Hotels (JRWalker, 13 May 2013)
4.5 of 5 stars 1 Vote
Chicago (coleman488, 15 Jul 2008)
4.5 of 5 stars 1 Vote
Baseball Park Reviews (baltoteach, 6 May 2008)
4.0 of 5 stars 6 Votes

Recent Trip

road trip usa (susie114, 12 Jun 2012)
4.5 of 5 stars 1 Vote
Family Fun!!! (lala74pa, 21 Jan 2008)
4.5 of 5 stars 1 Vote
Windy City Weekend (Chicago) (LVinWA, 20 Jun 2006)
4.0 of 5 stars 5 Votes