Chicago has been called many names – Windy City (for its politicians and lake winds), The City of Big Shoulders (for its unions), The Second City (used to be by population, but now 3rd after NY and LA), Chi-Town, etc. I would call it the city with a big heart – friendly people, diverse neighborhoods, some of the best medical and charity organizations in the country – and of course its welcoming attitude. Just look at the tagline the Mayor’s office came up with: “We’re glad you’re here”. My first impression of Chicago was from a travel encyclopedia some 30 years ago, and I was just fascinated by the “Corn Cob” buildings on the river. The real deal was amazing. With its unique architecture, natural beauty of the lake and forest preserves, eclectic mix of neighborhoods, great jazz and comedy, this is by far my favorite city in the world. Here are a few of my picks around town.
The Lake
Chicago is situated right on Lake Michigan, the largest of the Great Lakes. Locals love spending time by the lake. You’ll see a lot of bikers, roller-skaters, runners, walkers, swimmers, volleyballers and just about anyone trying to get some sun here. While Chicago winter is absolutely brutal, it’s only 3 months of the year – the rest, particularly May through November, is beautiful. North Avenue Beach, just north of the Magnificent Mile downtown, is an excellent place to take a walk or sit down for a drink by the lake. Alike the Muscle Beach in Santa Monica, CA, there is a gym right on the beach during the summer months. You will see chess-players relaxing in the shade and plenty of youngsters sitting on the rocks by the water. The Lake is also an important navigation point – it’s East, so you will always know your way west.
Where to have a bite on the Lake: Castaways which looks like a boat, with its lake breeze and magnificent views, quick sandwiches and drinks and great people watching.
Navy Pier
Chicago’s Navy Pier is one of the gems on the lake, and yes, a popular touristy attraction. It used to be a naval base and still welcomes many ships. There are plenty of attractions here for the kids – a Ferris Wheel with spectacular views of the city, a variety of rides and mazes, and plenty of sweets. Navy Pier is often home to large shows, including the Internet conventions and a big Gardening show.
The ballroom at the end of the Pier is popular for weddings and is one of the best New Year’s parties in the city. There are several boats, such as the Odyssey, parked along the pier where you can take a nice evening (or lunch) cruise around the lake offering city views, food and entertainment. Dress up for an evening cruise. I would highly recommend a Chicago boat cruise. You can hop aboard one either at Navy Pier or by the Wrigley Building on Michigan Avenue. These tours will tell you a lot about Chicago history and architecture and the ride is absolutely gorgeous, going along the Chicago River and into the lake. A Chicago boat cruise is a great way to start your visit, so you can see where you want to focus next. Pick a day when it’s not too cold or windy, or bring a jacket. Never underestimate the Chicago wind. You can quickly get to Navy Pier by cab from downtown or catch a free trolley on Michigan Avenue.
Where to have a bite at Navy Pier: Joe’s Be-Bop Café & Jazz Emporium with live Chicago jazz seven days a week and delicious ribs, chicken and jambalaya.
Michigan Avenue and Grant Park
Who hasn’t been to Chicago and not stepped foot on Michigan avenue? It’s Chicago’s pride and joy – home to some of the tallest skyscrapers, excellent shopping, majority of businesses and some nice parks. It is the location of the Water Tower – one of the few structures, along with nearby Newberry Library, which survived the Great Chicago Fire of 1871 that practically wiped out the city and its buildings. Don’t mix the quaint little building with the nearby Water Tower mall, a popular shopping destination. Another important architectural piece here is the Hancock building – the 3rd tallest building in the city (following the Sears tower and AON). I always bring my out-of-town guests to the Signature Lounge – a bar on top of the Hancock building (not to confuse with a very expensive Signature Room restaurant, just a floor below). The great thing about the Signature Lounge is that you have a 360 view of the city (go on a clear night) and all it costs is a price of a delicious Martini. You can also take a carriage ride along the street and down to the boutique-filled Oak street for a romantic night. The area between Oak Street and the Chicago River is known as the Magnificent Mile. Walk south down the Magnificent Mile and stop right along the bridge to take in the beauty of the Chicago Tribune and Wrigley buildings – these structures are some of Chicago’s architectural legacy.
Further down is the Chicago loop and Grant Park. Grant Park has been completely renovated in recent years. There is a historic Buckingham fountain – one of the most beautiful water structures. There is also the Milennium Park on the edge of Grant Park with newly built Crown fountain that kids just love playing and splashing around. And, of course, the famous Bean (officially called Cloud Gate) – a stainless structure that reflects off the city and the people walking by – truly a unique installation. Grant Park is the location for many of the city’s festivals – and summer is just chock-full of them. Some of the most popular ones are the Taste of Chicago (usually around July) featuring the city’s best restaurants, the Blues fest in spring and Jazz fest in the fall, lots of musical performances throughout summer. Dancing in the park, which happens every week in the summer, is great fun – instructors will teach you a style of dance (such as salsa) and then you can apply your new skills dancing to a live band. Other festivals include the Air and Water show which happens early to mid-August and the Venetian fest- usually end of August – with a variety of decorated ships and plenty of food and music. Chicagoans sure know how to have a good time. Get more detail on the city events at chicagofestivals.net.
Where to have a bite on Michigan Avenue: majority of good restaurants are a little east, in the Rush/Division area. However, I love my pick for Michigan Avenue – Bandera with excellent fire-roasted chicken, super-yummy salads, home-made corn-bread, live music and view of Michigan Avenue.
The Loop and Theater District
A little further from the Lake is the Loop – Chicago’s downtown away from Michigan Avenue – this is where the city began. It’s called the loop for its geographic borders. Here you will find the 0 point of the city – State Street and Madison – State Street is the 0 point between East and West streets and Madison Street is the starting point for North-South numbers. The loop is graced by many of the city’s skyscrapers and architectural marvels. Some of the highlights are the art-deco Chicago Board of Trade (LaSalle/Jackson streets) and the Civic Opera House (Wacker Drive), the tallest building in the US, the Sears Tower (on Wacker Drive) and the futuristic Thompson center (Randolph/Clark). Many artists gifted the city with their works displayed around the loop – Picasso, Miro, Chagall, Calder, to name a few.
The famous Chicago Theater District is located in the loop. Many Broadway productions start here, testing the waters before their New York run. Come fall, many Chicago theaters will be abuzz – from the Auditorium Theater, to LaSalle Bank Theater, Cadillac Palace Theater. Many of these are worth a trip not just for the production but for a look at the design and architecture inside the theater. Many of the city’s parades start in the Loop, especially the incredibly popular St.Patrick’s Day parade (South side of the city has the main event, but this one is big too). Chicago has a huge Irish heritage, so not only is the Chicago River colored green for the day, there are parades, and everyone feels Irish.
A great experience in the city’s loop is hopping on the L (the elevated city train system). Take a ride to see the inner city or travel around Chi-Town – it’s extremely easy to use and you can buy a transfer to use on the plentiful city buses as well. Chicago has user-friendly transportation. If you don’t have too much luggage, you can also use the L to go to and from the airport (both O’Hare and Midway) – a much faster ride than a cab in the infamous city traffic.
Where to have a bite in the Loop: A great pick before theater is Petterino’s where you can see caricatures of celebrities on the walls and great steak on the table.
Chicago Neighborhoods
Step a little further from downtown and you will discover a plethora of eclectic neighborhood, representing every age, culture and tradition. Lincoln Park is a popular residence for the Chicago yuppies – lots of starting professionals and young metropolitan families. The area is named after the neighboring park – one of the most beautiful and the largest in the city, right by the Lake.
Take a stroll in the park, stop to feed the ducks in the pond, watch the butterflies in the Conservatory, or visit the Lincoln Park Zoo. The zoo is open year-round and free to all. It is a fairly large zoo and there are also areas dedicated to kids – Farm in the zoo (a large feeding and petting area) and Pritzker Family zoo. You can also try a paddleboat in the lagoon – great views of the downtown skyline from there.
Where to have a bite in Lincoln Park: Geja’s cafe on Armitage for its scrumptious fondue, romantic atmosphere and live Spanish guitar.
A little southwest of Lincoln Park is the Old Town neighborhood. It used to be the center of the hippie culture in the 60s and still has a very artsy feel. Old Town Art Fair is one of the best such events in the city and the oldest in the country.
The area is now very affluent and full of sprawling condos. It is also home to the Second City Comedy theater, which Chicago is so well known for, giving start to Mike Meyers, Bill Murray, John Belushi, Alan Arkin, Tim Meadows, Steve Carell and Tina Fey, to name a few. Just a few blocks south from Second City is Zanies – a great place to see live improve comedy, as long as you are up for being made fun of. If you are in Chicago, you have to see some good comedy and jazz – two of Chicago’s finest.
Where to have a bite in Old Town: One of the city’s best Mexican restaurants – Adobo Grill on Wells street, right next to Second City, with tableside guacamole making, amazing Margaritas, beautiful decor and an upscale take on Mexican cooking.
Further north of Old Town and Lincoln Park is Lakeview – a more affordable city living by the lake and parks. One of Lakeview’s best highlights is the Wrigley Field where the Chicago Cubs play. You will find many fans in and around the field; the most loyal ones take residence in the area. The statue of Chicago favorite baseball broadcaster, Harry Caray is right at the front reminding of the finest years in the city’s baseball history. Northsiders and the rest of Chicago cheer for the Cubs year after year.
Where to have a bite in Lakeview: you have to grab a hot dog at the Wrigley Field – just for the experience.
Bucktown is a hipster modern area west (take the blue line L to Division). Walk around funky stores and restaurants, or check out some galleries. This area is a great reflection of Chicago’s diversity. Despite the upscale metro feel, there are many hundred-year-old buildings and cobble streets. Each September the area hosts Around the Coyote creative festival which best demonstrates the spirit of this funky locale.
Where to have a bite in Bucktown: Le Bouchon on Damen is a quaint and unique authentic French bistro, favored by the locals, with scrumptious duck and unbelievable steak frites.
Landmarks worth a stop
You can spend a week in Chicago and still not run out of things to do. It’s impossible to list them all here, but here are a few other points to see:
- The Art Institute, on Michigan Avenue, right next to the Millennium Park, with a great impressionist collection and unique visiting exhibits.
- Museum of Science and Industry, particularly the Water geyser area
- Shedd Aquarium – perfect for kids and adults – with Caribbean reef, Oceanarium, Komodo dragon and more. On Thursdays during the summer catch Jazzin’ at the Shedd – listen to live music sipping drinks on the Aquarium open terrace on the lake.
- Oak Park area with Frank Lloyd Wright houses and interesting tours. Take the blue line to Oak Park.
Chicago Jazz
Chicago Jazz is an institution and the city is sprawled with top-notch jazz clubs and quaint dives. You can hear different styles, and see completely different crowds. Some of my favorites include Andy’s Jazz Club, the Underground Wonder Bar, Green Dolphin Street, and the one you should not miss:
The Green Mill. Located in Uptown, on the corner of Broadway and Lawrence, this is one of the oldest Chicago jazz clubs, frequented in the past by Al Capone and Marilyn Monroe. There are different performances each night, from Swing Shift Orchestra to Kimberly Gordon, jazz festivals and Uptown Poetry slams. But my absolute favorite is the Sabertooth quartet, playing improv after Midnight on Saturdays. Their rendition of Mulatu Astatke’s “Yekermo Sew” is the best I’ve heard. Get here early to get a seat – the place is small and gets crowded quickly. Green Mill has a special vibe and is like no other, just like the city of Chicago, a gem on the lake.
