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Fun Places to Visit in Chicago, Illinois, Milwaukee, Wisconsin Dells, Madison

Things to do / Travel Guide

If you think Chicago is the only draw for this region, you'll be pleasantly surprised by how much else the region has to offer. There is a lot to do in the Windy City, but the other cities like Milwaukee and Madison, and the resort areas like Lake Geneva and Wisconsin Dells, will charm you and fill your days as well.

Indiana Dunes

Located in Northern Indiana, the 15-mile-long stretch of shoreline that hugs Lake Michigan from Gary, Indiana to Michigan City, Indiana is just one of the beautiful aspects of the Indiana Sand Dunes. The dunes are not just about fun in the sun on the beautiful beaches; there are also bogs, swamps, and woodland forests where you can camp, hike, and bike ride.


Chicago is as diverse in its citizens as it is in its attractions. Known for being the friendly big city, you get the big-city feel without the big-city attitude. The majority of Chicago's attractions are located in the lively and large downtown area. More so than in other metropolises, Chicago is split into very distinct communities, with a number of major tourist areas. Many communities are split into smaller distinct neighborhoods. Unlike other big cities, these community areas are often self-sufficient, and each one has its own feel and ethnic past.

You should become acquainted with the following community areas, at least. You can take several hours strolling around to get the hang of each one, at least. Your least worry is running out of places to explore.

Chicago's downtown core is known as the Loop - for the EL (train system) tracks that encircle it. Bordered by the Chicago River to the north and west and Lake Michigan on the east, the Loop is known as the historical center of Chicago as well as the largest business area in the United states after Manhattan. Most of Chicago's soaring skyscrapers, starting with the Sears Tower, are located in the Loop. (The others are just north of the Loop.) The eastern side of the Loop is park: Grant Park, Chicago's front yard, and Millennium Park, home of some fantastic Frank Gehry and Anish Kapoor installations.

Just north of the Loop, across the river, you'll find the extravagant shopping district generally known as the Magnificent Mile; it's located primarily on Michigan Avenue. You may actually find some reasonably priced Chicago motels here.

Around the Loop all the Chicago communities and neighborhoods fan out, to the north, west, and south. To the north you've got north side and far north side. Remember these names, as they're a big help when asking for directions or trying to orientate yourself. Here are the most famous or oft-visited places to the north of the Loop:
  • Near North Side - This community boasts almost as many goodies as the Loop itself. Here's where you'll find the Magnificent Mile, Navy Pier, many of the city's best pubs, entertainment, and restaurants, great theater, and the city's best improv. North Michigan Avenue and West Chicago Avenue both run through Near North Side.
  • Gold Coast - This neighborhood, actually located within Near North Side, is famous for its opulent architecture and standard of living. Numerous high-rise apartment buildings populate its blocks, mostly along Lake Shore Drive on Lake Michigan.
  • Lincoln Park - This north side community is named for the park of the same name that spans a stretch of the Lake Michigan shore. In the second half of the 20th century many Puerto Ricans moved in, but more recently this ethnic group has largely moved on, and young professionals and young families, and with them boutiques, restaurants, and coffee shops, have moved in. North Lincoln Avenue runs through this community.
  • Logan Square - Another diverse north side community undergoing gentrification. Recently artists have begun moving in, bringing with them the requisite art, boutique, and coffee shops. North Milwaukee Avenue and West Fullerton Avenue are two main streets in Logan Square.
  • Bucktown - Where goats (bucks) used to graze, today you can take your pick of a large number of restaurants and dance clubs. It's actually a neighborhood within Logan Square, bounded on the west by Western Avenue.
  • Uptown - Centered around Broadway, this is the region's, and the city's, concert venue district. Chicago's historic gangsters are also tied to this area, and as an added attraction, Argyle Street is lined with Asian restaurants and groceries. It's located in the far north side.
  • Rogers Park - Located in the far north side, this is one of the most diverse communities in America, with more than 80 languages spoken within its borders. Haitians and Sub-Saharan Africans live side-by-side with Hispanic- and European-Americans. North Clark Street is one of its main streets.
All the following communities and neighborhoods are located to the south of the Loop, either immediately near the Loop, in the south side, the southwest side, the far southwest side, or the far southeast side.
  • Near South Side - home to Museum Campus Chicago, with great family-friendly museums, and the Prairie Avenue Historical District, with a showcase of Frank Lloyd Wright architecture. Just south of Museum Campus is Soldier Field, home to the Chicago Bears.
  • Bronzeville - This south side neighborhood is the center of African American Chicago, populated by African Americans since the beginning of the Great Migration in the early decades of the 20th century. It's filled with culturally-significant landmarks. South Michigan Avenue runs through it.
  • Bridgeport - Home to Irish, Lithuanian, and Mexican immigrants, this south side community is one of Chicago's oldest, with large swathes preserved for curious visitors. Stevenson Expressway South girds it to the north, and South Halsted Street runs north-south within it.
  • Back of the Yards - Site of Upton Sinclair's “The Jungle,” this southwest side neighborhood was one of Chicago's famous packinghouse centers. Today its home to a diverse scene with plenty of nightlife attractions. Look for West 47th Street.
  • Hyde Park - This community is located in between Lake Michigan and Washington Park. It's where the University of Chicago is located, plus several middle and upper class neighborhoods where a number of famous people have lived: Muhammad Ali and Barack Obama have both lived here. Look for South Woodlawn Avenue and Midway Plaisance Park.
  • Beverly - This hilly, far southwest side community has one of the largest historic districts in the U.S. It's had a colorful Irish past, and today boasts more Irish pubs than any other place in Chicago. West 87th Street and South Ashland Avenue run through it.
  • Hegewisch - “Heg-wish” for non-Chicagoans. Surrounded by wetlands and bordered by train tracks, this neighborhood is like being in a small town in the middle of the big city. You can still fish in nearby Lake Calumet, Calumet River, and Wolf Lake.
  • These are some neighborhoods in Southside Chicago that tourists would be wise to avoid: Riverdale, Roseland, and West Pullman. Neighborhoods to stay away from at night include Englewood, Eastern Morgan Park, Marquette Park, Pullman, East Chicago, Brainerd, and Gresham.
These next communities all fall to the west of the Loop. Ethnic Chicago is centered in these parts of the city.
  • Greektown - While many of the ethnic Greeks have left the area, bars and Greek restaurants remain. This near west side neighborhood is where “My Big Fat Greek Wedding” took place (though it was filmed elsewhere).You'll find a lot on Halsted Street.
  • Little Italy - Same as Greektown, there are many Italian restaurants but few Italians. You can find the National Italian American Sports Hall of Fame in this area. It's also a near west side neighborhood, along Taylor Street.
  • Wicker Park - After many ethnic transformations, from German and Swedish to Polish and Puerto Rican, the west neighborhood has recently proved hospitable to artists and hipsters. North Milwaukee Avenue and North Damen Avenue run through the neighborhood.
  • Ukrainian Village - This other west neighborhood contains many historic Ukranian landmarks, like churches. Coffee shops, clothing stores, art galleries, and neighborhood cafes fill the major streets. North Damen Avenue runs through Ukrainian Village.
  • Oak Park - This far west suburb is where Frank Lloyd Wright perfected his Prairie School style, and it's home to the largest amount of homes and buildings by the architect in the world. Eisenhower Expressway runs through the suburb, and Roosevelt Road is a major thoroughfare.


Racine, in southern Wisconsin, is known for many Frank Lloyd Wright houses and buildings, and where the children's book publisher Little Golden Books is based.

Milwaukee, WI

Milwaukee, Wisconsin is made up mostly by smaller towns that are now incorporated into the city. The smaller towns, with hard to pronounce names like Wauwatosa, Waukesha, and Greenfield, were created in the 1800's by rival settlers. The main district in Milwaukee is the Historic Third Ward. A one-time warehouse and manufacturing district, is now the place to go for shopping. Originally rival towns, Juneautown and Kilbourntown now compete for patrons' business, with a multitude of bars and clubs to keep up your dancin' feet. West End is where Harley-Davidson keeps their corporate headquarters, and where Miller Brewing Company keeps their brew factory.

Riverwalk, along the Milwaukee River, is connecting people back to the Milwaukee River with shops, restaurants, and boating docks along a beautiful promenade. Riverwalk's service is to remind folks of the old-world charm Milwaukee has to offer.

One of Milwaukee's monikers is the “City of Festivals,” because of the large amount of year-round ethnic festivals held in the city. The greatest of these, which holds the Guinness title for largest music festival in the world, is Summerfest, held in late June-early July along the Milwaukee.

Sheboygan, WI

There's a large concentration of golf courses and spas in this city along Lake Michigan. Whistling Straits, which some call America's best course, is located near Sheboygan.


Madison is situated between and on either side of Lake Mendota and Lake Monona, about three and a half hours from Chicago, and 90 minutes from Milwaukee. The central isthmus that separates the two lakes is home to the Capitol Building - smack in the center of the isthmus, and the city's downtown. The South West section is home to the University of Wisconsin, while Near West is more of the suburban area. Madison is often rated one of the nicest places in the U.S. to live.

The University of Wisconsin-Madison is situated on the shores of Lake Mendota just west of the State Capitol Building. On the Lake Monona side of the isthmus is the Monona Terrace, with amazing views of downtown Madison. For a night out on the town, head near the State Capitol building around Main Street, the pedestrian-only State Street, and King Street.

Lake Geneva

Lake Geneva is primarily a resort town, and has been one since the late 19th century. Where else can you visit orchards and petting zoos, parasail, and take a carriage ride in one day? Lake Geneva is set southwest of Milwaukee and is clustered with as much quaint charm as an old-time ice cream parlor!

New Glarus

America's “Little Switzerland” has been keeping the Swiss tradition alive for over 150 years! Situated southwest of Madison, New Glarus is a hidden gem were you can watch weavers works their magic, dine on Swiss cuisine, and get an intimate look at what old-world Swiss immigrants brought to Wisconsin.

Wisconsin Dells

The Wisconsin Dells are known mostly for their indoor and outdoor water parks and family-friendly atmosphere. It is located northwest of Milwaukee. Along with the water parks, there is a plethora of outdoor activities like hiking trails and horseback riding.

Places to Visit in Chicago, Illinois, Milwaukee, Wisconsin Dells, Madison

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