Travel Rankings & Advice

Chicago Travel Guide


"It is hopeless for the occasional visitor to try to keep up with Chicago. She outgrows his prophecies faster than he can make them." Although he made up his mind about the Windy City before it even reached its 50th year, Mark Twain's impression of Chicago has proven long-lasting. America's third-largest city has been described in a myriad of ways throughout its lifetime. When Thomas Edison and Nikola Tesla were competing for the ... continue» Read More

Best Airfares to Chicago

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When to Visit Chicago

The best times to visit Chicago are April through May or September through October, when the temperatures are warm and hotel rates are reasonable. You'll also find a lot of festivals taking place in spring and fall. Summer marks Chicago's peak tourist season, with travelers from around the country hoping to take advantage of the warm weather. If you're planning to visit the Windy City between June and August, prepare yourself for denser crowds and higher prices on accommodations. Winter is a different story altogether: Chicago experiences bitter temperatures between November and March, but if you can hack it, hotel and airfare deals are easy to find.

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Getting Around Chicago

Chicago Neighborhoods

Chicago's eastern boundary is formed by Lake Michigan, and the city is divided by the Chicago River into three geographic sections: North Side, South Side and West Side. These sections surround the city's compact downtown area, the Loop.

The Loop

Accessible via all "L" lines

Located near the shores of Lake Michigan, the Loop refers to a group of high-rise buildings within a rectangular loop of elevated train tracks. As the city's central business hub, the Loop offers visitors a taste of a bona fide big-city experience. Here, you'll find the Willis Tower (formerly known as the Sears Tower), the second-tallest building in North America. Most hotels and restaurants located in this area cater to business travelers: Lodging here verges on the high-end and luxury side, and many of the dining establishments are Michelin-starred. If you are looking for lower price tags or to enjoy the city's nightlife, consider bedding down north of the Loop; this area is generally quiet after dark.

The North Side

The North Side is home to many of the popular tourist attractions, including the Magnificent Mile, and it's where many of the city's best hotels and shops are found. The North Side is also home to the city's most popular, touristy and residential neighborhoods.

Near North: The Magnificent Mile & Streeterville

Accessible via the Red Line's Grand-Red and Chicago-Red "L" stops.

Extending north from the Loop is the Magnificent Mile, a stretch of Michigan Avenue (the main downtown thoroughfare) lined with big-name department stores and luxury retailers. You'll also find several notable hotels — including the Park Hyatt and The Drake — along this bustling thoroughfare.

Just east of the Magnificent Mile is Streeterville, an area well-versed in entertainment. This is where you'll find Navy Pier, a popular family hangout thanks to attractions like the Chicago Children's Museum and a 15-story Ferris wheel. This neighborhood isn't just for kids, though: More mature travelers come here to take advantage of the diverse culinary scene and the artsy venues, including the Museum of Contemporary Art and the Chicago Shakespeare Theater. Streeterville also encompasses Ohio Street Beach where Chicagoans come to relax during the steamy summer months. Although many hotels in this area are designed for business travelers, families and budget-minded travelers will find a few options here that will suit their needs.

River North

Accessible via the Red Line's Grand-Red "L" stop and the Brown and Purple lines' Merchandise Mart "L" stop

Located across the Chicago River from the northwest corner of the Loop (directly west of the Magnificent Mile), the River North district was once a primarily industrial area. Now, all of the neighborhood's factories and warehouses accommodate innovative gallery spaces, art studios and and trade showrooms. River North is also a gathering spot for foodies: Restaurants here serve everything from raw oysters to Spanish tapas to barbecue ribs. Area hotels are trendy as well, with big-name properties like the Trump International Hotel & Tower laying claim to space here. But there are also several boutique options, as well as a smattering of more affordable lodging options.

Gold Coast

Accessible via the Red Line's Clark/Division "L" stop

Michigan Avenue continues north along the lake into Gold Coast neighborhood. Much more demure than Streeterville to the south, the Gold Coast is home to some of Chicago's most desirable real estate, including a number of historic mansions, as well as high-end shops and luxury hotels like the Waldorf Astoria Chicago. This part of town also has a bit of a wild side: Once the sun sets, make your way to Rush Street for your choice of nightlife venues.

Old Town

Accessible via the Brown/Purple Lines' Sedgwick "L" stop

West of the Gold Coast is Old Town, which earns its name from the historical brick alleys and Victorian architecture. Old Town has long acted as a mixing bowl for Chicago's varied population: While exploring this neighborhood, you're bound to encounter young professionals, immigrants and members of the LGBT community. If you can, spend an evening at Old Town's Second City comedy club, where famous comedians like Tina Fey and Steve Carell got their start. But don't plan on bedding down here; when it comes to hotels, Old Town is lacking.

Lincoln Park

Accessible via the Brown/Purple Lines' Sedgwick and Fullerton "L" stops and the Red Line's North/Clybourn "L" stop

The Lincoln Park neighborhood includes both the park itself and the residential streets located west. Inside the park — which runs along the edge of Lake Michigan — is the Lincoln Park Zoo, one of the oldest zoos in the country and a popular (and free) family attraction. The park also features the extensive North Avenue Beach (a nice spot for sunbathing during the warmer months) and the Lakefront Trail, which traces the beach as it makes its way from the Edgewater neighborhood to the north down to Navy Pier. The area just west of the park includes a lot of residential areas, but you'll find plenty of shops and restaurants along Armitage and Lincoln avenues, as well as on Clark Street. Lincoln Park also encompasses the nationally acclaimed Steppenwolf Theatre, which sits on North Halsted Street near the North/Clybourn metro stop.

As far as hotel options go, Lincoln Park doesn't have a lot of variety. You'll find a handful of budget friendly hotels, as well as a few B&Bs.

Wicker Park & Bucktown

Accessible via the Blue Line's Damen-O'Hare and Western-O'Hare "L" stops

If you tire of the big-name stores along the Magnificent Mile, check out the independent bookstores, art galleries and boutiques scattered throughout Wicker Park and Bucktown. Sitting west of Lincoln Park, this part of town is Chicago's creative epicenter; the Wicker Park and Bucktown districts teem with art galleries, many of them located in the Flat Iron Arts Building on North Milwaukee Avenue. This part of town is also contributing to Chicago's reputation as a foodie destination, with celebrated restaurants serving everything from Midwestern specialties to Nepalese fare. The area's hotels, on the other hand, are not nearly as glamorous as its arts and dining scene. Rather, Wicker Park and Bucktown lodging is better described as homey, with several B&Bs to choose from.


Accessible via the Brown, Purple and Red Line's Belmont "L" stop and the Red Line's Addison and Sheridan "L" stops

Just north of Lincoln Park is Lakeview, a lively neighborhood home to a variety of restaurants, stores and entertainment venues. Make your way to one of the areas four main commercial thoroughfares — Clark Street and Lincoln, Belmont and Broadway avenues — if you're interested in shopping or nightlife. Here, you'll also find a smattering of independent theaters. But the Lakeview area also provides some respite from fast-paced city life: The neighborhood encompasses the swath of Lincoln Park that's home to the 8-acre Jarvis Migratory Bird Sanctuary, and away from the commercial districts, you'll find leafy residential areas (as well as a smattering of independently owned B&Bs.

Boystown & Wrigleyville

Accessible via the Brown, Purple and Red Line's Belmont "L" stop and the Red Line's Addison "L" stop

Within the eastern part of the Lakeview area (just west of the neighborhood's section of Lincoln Park) is Boystown. Despite this district's small size, Boystown accommodates one of the country's largest LGBT communities. This is where the city's raucous Pride celebration takes place each year; but if you can't make it to the festival, be sure to check out the Center on Halsted, the neighborhood's thriving community center. You'll also find an abundance of restaurants here serving everything from Spanish tapas to specialty desserts. As far as lodging goes, you won't find many hotels to choose from, but that may be a good thing: Boystown is known for its raucous nightlife.

Continue west of Boystown and you'll reach Wrigleyville. This little pocket of central Lakeview earns its moniker from its proximity to Wrigley Field, the second oldest ballpark in the country and home of the Cubs baseball team. The streets surrounding the stadium are packed with sports bars and stores selling Cubs memorabilia. Wrigleyville's entertainment and nightlife options also include comedy clubs and live music venues — you'll find the best selections along Clark, Addison and Sheffield avenues.

Uptown & Andersonville

Accessible via the Red Line's Wilson, Lawrence, Argyle, Berwyn and Bryn Mawr "L" stops

The Uptown neighborhood just north of Wrigleyville was Chicago's go-to spot for debauchery during the 1920s and 1930s. Since then, Uptown has seen its glory fade, but revitalization efforts are once again luring locals and travelers to this northern neighborhood. Many of the area's old art deco buildings are being refurbished, and although Chicagoans once flocked to the bars here because they sold liquor during Prohibition, Uptown's watering holes are now popular for their live music and dancing. This neighborhood is also earning nods of approval for its eateries, with restaurants along Argyle Street serving everything from Vietnamese cuisine to Middle Eastern specialties.

Continue north of Uptown and you'll find yourself in quirky Andersonville. Like Uptown, Andersonville boasts thriving culinary and nightlife scenes, but this area is also known for its diverse population. At the heart of Andersonville you'll find the Swedish American Museum; in addition to the museum, Andersonville encompasses a host of LGBT-friendly bars, independently owned businesses and even a craft brewery. And although you won't find many lodging options in Uptown, you will come across a couple B&Bs in Andersonville.

Edgewater & Rogers Park

Accessible via the Red Line's Thorndale, Granville, Loyola and Morse "L" stops

Located along the Lake Michigan shoreline, Edgewater draws Chicago's resident beach-lovers to its vast stretches of sand. This part of town is also quite popular with families thanks to its parks, as well as its historic enclaves. Bryn Mawr is perhaps the most well known of these: Bryn Mawr Avenue is lined with old-fashioned street lamps and a bevvy of 1920s architecture. It should come as no surprise that Edgewater is also well known for its antique shops

North of Edgewater is Rogers Park. Chicago's northernmost neighborhood is also one of its most diverse. The area — which encompasses Loyola University's campus — boasts an eclectic population made up of Asians, East Indians, Germans and Russian Jews, all of whom have left their mark on the community, especially in cuisine. Restaurants surrounding the university serve specialties from all around the globe.

The West Side

Chicago's West Side is a cultural melting pot, housing Greek, Mexican and Puerto Rican communities, among others. Although West Chicago is more residential than the Loop and the neighborhoods immediately north of the Loop, the districts on the Chicago River's west bank are worth exploring — especially if you like to eat.

West Loop

Accessible via the Blue Line's Clinton-Blue "L" stop and the Green and Pink Lines' Clinton-Green "L" stop

As its name suggests, West Loop sits immediately west of downtown Chicago. This former industrial area is now one of the city's edgiest, with former factories and warehouses sheltering galleries, boutique shops and restaurants. For a wide selection of bars and eateries, head to Randolph Street: Nicknamed "Restaurant Row," this thoroughfare near the Fulton Market is lined with bars, bakeries, breweries and a host of dining venues. Meanwhile, interspersed between the trendy condos along West Monroe Street and the Dwight D. Eisenhower Expressway are the Hellenic craft stores and lively tavernas of Greektown. In addition to good food and lively nightlife venues, Greektown also features the National Hellenic Museum, where you can learn more about Greek culture. Hotels are not as plentiful here as they are in downtown, but lodging in the West Loop does cater to a variety of budgets.

West Town

Accessible via the Green and Pink Lines' Morgan-Lake Ashland-Lake "L" stops and the Blue Line's Grand-Blue and Chicago-Blue "L" stops

To the north of the West Loop is West Town, home of Chicago's Ukrainian Village. This small section of town — bordered by North Rockwell Street, West Division Street, North Damen Avenue and West Chicago Avenue — features the Ukrainian National Museum, some interesting 19th century architecture and a smattering of interesting shops, restaurants and bars. West Town (the Ukrainian Village included) exudes a low-key, youthful vibe with interesting vintage boutiques, up-and-coming brunch spots and plenty of coffee shops. Lodging is limited here, so consider staying in the Loop and crossing the river when you want to visit.

Humboldt Park

Accessible via bus Nos. 52, 65, 70, 72 and 94

Continue east from West Town and you'll reach Humboldt Park, Chicago's Puerto Rican district. Every June, this part of town puts on a lively Puerto Rican People's Parade, which attracts more than a million spectators. During the rest of the year, Humboldt Park lures visitors with its Puerto Rican cuisine, local shops and various cultural institutions, such as the Institute of Puerto Rican Arts & Culture. The neighborhood is just as vibrant as its residents, with many of the buildings featuring colorful murals.

Little Italy

Accessible via the Blue Line's UIC-Halsted and Racine "L" stops and the Pink Line's Polk and 18th Street "L" stops

If you've come to Chicago for the pizza, head south of the West Loop into Little Italy. Also known as the University District because of its proximity to the University of Illinois at Chicago campus, Little Italy is the place to go for a plate of pasta or a slice of pie. Some of the restaurants here have been handed down from generation to generation. But Italian isn't the only cuisine represented here: This is also the place to go for a bite of Polish sausage. Head over to the Maxwell Street Market on the eastern edge of the UIC campus for sausages and other street foods.

Because of demand from the university, you will find some hotels here — but not nearly as many as you would if you looked in the Loop or neighborhoods just north of the Loop.

Lower West Side & Little Village

Accessible via all Pink Line "L" stops between 18th Street and 54th/Cermak

If you go to the West Loop for Greek food and Little Italy for Italian fare, continue south to the Lower West Side for Mexican specialties. Also known as Pilsen, this part of town has long acted as a home base for immigrant communities. Although it was originally dominated by Europeans, somewhere in its 150-year-long history, the population of the Lower West Side shifted; today, the area comprises vintage shops, relaxed cafes and numerous bodegas serving up authentic Mexican dishes. In between shopping and dining, take a peek at the incredible murals that grace the walls throughout this neighborhood. You'll even find some in the 18th Street "L" station.

Continue east from the Lower West Side and you'll find yourself in Little Village, another primarily Mexican-American district. Like its eastern neighbor, Little Village is a great place to go to sample authentic South-of-the-Border cuisine.

The South Side

You'll find several of Chicago's most popular things to do sitting just south of the Loop, but areas even further south have garnered a bad rep. Once a hot bed for Prohibition-era crime, South Chicago has long played the backdrop to gang violence and crime. But this section of the city is experiencing a renaissance: Now, the South Side features some of the city's fastest growing residential neighborhoods, as well as fascinating pockets of culture.

South Loop

Accessible via the Red Line's Harrison "L" stop, the Blue Line's LaSalle "L" stop and the Green, Orange and Red Lines' Roosevelt "L" stop

Just south of the Loop, this part of Chicago attracts tourists and locals in droves. The South Loop has a little something for everyone. It's here that you'll find the largest chunk of Grant Park and the city's Museum Campus, home to such popular attractions as the Field Museum, the Shedd Aquarium and the Adler Planetarium. (Grant Park also hosts some of the city's liveliest festivals, including the Chicago Blues Festival and Lollapalooza.) Just south of the Field Museum is Soldier Field where the NFL's Chicago Bears play, while heading south of the Adler Planetarium will lead you to the Northerly Island beach and nature area. Head west of Lake Michigan to South Michigan Avenue and to see the mansions of Millionaire's Row, where Chicago's richest residents lived during the late 19th century. Even further west is the trendy Printer's Row area, where boutique shops and small theaters rub elbows with a cornucopia of restaurants, bars and live music venues. The South Loop also encompasses McCormick Place, the largest convention center in the country.

Given that the convention center can be found here, South Loop hotels (including the Hilton Chicago and the Renaissance Blackstone) cater to business travelers. But leisure travelers and families will find several independent properties (like Wheeler Mansion), as well as budget-friendly options.


Accessible via the Red Line's Cermak-Chinatown "L" stop

A walk down South Wentworth Avenue will lead you past a smattering of dim sum restaurants and tea houses, not to mention the colorful gate marking the entrance to Chicago's Chinatown district. This lively (albeit small) part of town houses a dense Chinese population — the members of which have left their mark on the area's appearance. Between the pagodas in Ping Tom Memorial Park and the terraced rooftop of the Chicago Chinese Cultural Institute lies a variety of Asian grocery stores and craft shops. You'll also find interesting zodiac-influenced art throughout Chinatown Square, a plaza surrounded by restaurants and shops.


Accessible via the Green Line's 35-Bronzeville-IIT, Indiana, 43rd Street, 47th-Green and 51st Street "L" stops

During the early 20th century, Bronzeville became a refuge for black Americans seeking to escape the persecution of the South. As a result, this South Side neighborhood experienced a cultural boom similar to the Harlem Renaissance, with such legendary people as civil rights activist Ida B. Wells and musician Louis Armstrong helping to nurture a strong political and artistic voice in the community. Tributes to Bronzeville's cultural icons — including sculptures and murals — can be found throughout the area, rubbing elbows with Victorian, gothic and Romanesque architecture. A tour of Bronzeville's cultural landmarks is an interesting way to spend an afternoon in Chicago, but a lack of lodging will make spending the night here difficult.


Accessible via the Milwaukee District North Line's 47th Street (Kenwood) Metra stop

Sitting south of Bronzeville along the shores of Lake Michigan is Kenwood, a fairly small neighborhood known for its expansive mansions. This part of town has been home to some of the city's most prominent residents, including Muhammad Ali and Muddy Waters. When you're not keeping your eyes peeled for historic homes, you can check out the exhibits at the Hyde Park Art Center or grab a bite to eat at Zaleski & Horvath MarketCafe, one of the most popular delis in the city. Kenwood also boasts some prime parkland as well as a few strips of beach.

Hyde Park

Accessible via the Green Line's 51st Street and Garfield-Green "L" stops and the Milwaukee District North Line's 51st/53rd Street (Hyde Park), 55th-56th-57th Street and the 59th Street (University of Chicago) Metra stops

Aside from the South Loop, Hyde Park is one of the most popular South Side neighborhoods among visitors. It was in this area that the famous 1893 World Fair electrified the city; the fairgrounds are now home to the Museum of Science and Industry, which overlooks Lake Michigan and the Columbia Basin from its seat in Jackson Park. This green space also features a couple of beaches, not to mention walking paths. Jackson Park is connected to Washington Park (home of the DuSable Museum of African American History) by the Midway Plaisance, a park-like promenade that runs the length of the neighborhood's southern border and frames the southern edge of the University of Chicago campus. The presence of the university has yielded a fairly affordable dining scene, as well as a handful of lodging options.


As you would in any big city, exercise caution when you're out and about. Keep your valuables with you at all times. Make sure to have a clear sense of your surroundings when traveling after dark, and avoid walking alone as much as possible. This especially rings true in the South Side, which, despite major revitalization efforts, hasn't been able to shake its intimidating reputation fostered by violence and gang activity. Neighborhoods like the South Loop, Kenwood and Hyde Park are less affected than areas west of Lake Michigan, where poverty is more prevalent.

The best way to get around Chicago is via public transportation — specifically the "L" train. Operated by the Chicago Transit Authority, the "L" (short for "elevated train") is cheap and easy to use. The CTA also operates an extensive bus system with routes servicing nearly every attraction, but the bus may be difficult for newcomers to navigate. There's also the Metra regional train system that makes stops throughout downtown Chicago. You can use public transit to reach the city from both nearby airports. O'Hare International Airport (ORD) sits just less than 18 miles northwest of downtown and can be accessed via the Blue "L" line, and Chicago Midway International Airport (MDW) is located about 11 miles southwest of downtown and can be reached using the Orange "L" line.

Getting Around Chicago»

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