The Second City: Chicago

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The land of Abraham Lincoln, Al Capone, Bill Murray, and Walt Disney. With a guest-list this stacked, Chi-town packs a bunch so you'd better be prepared to see and do a lot. But in fairness to the minnow-cities of America, it's unjust to list the famous citizens of Chicago, for everybody who is anybody had to have stepped foot in this metropolis at one point or another, whether they dropped straight from the womb or simply made their name here. It's also why O'Hare Airport is the second busiest airport in the world and the Windy City has more highways passing through it than any other in the country. It's cemented its reputation as the foremost expert on improv comedy, known as a hotspot for jazz and blues, and is the breeding ground for skyscrapers with penthouses only affordable to someone who OWNs a cable network and is simply known by her first name. In a city that boasts as many nicknames as this, it's best to come with an itinerary, a fork, and a camera, for you will see, eat, and capture more memories here than anywhere else in America.

You should start in the popularly dubbed "Loop", the downtown area where most of the attractions are situated. You'll likely pay a premium for hotels in this area, so look into the neighboring suburbs to avoid breaking the bank. The nearby Northbrook is an easy drive into the city, and the Renaissance North Shore hotel (933 Skokie Blvd) here is always fairly priced at less than $70 per night for a 4-star lodging; with a chic decor, modern vibe, impeccable cleanliness, and great service, this is the best value around town. If you must stay in the Loop, dish over $100 a night plus $20 or so more for parking and stay at the River Hotel (75 E. Wacker Dr), perfectly located on the Riverwalk with a contemporary interior design and an amazing view overlooking the waterfront towards Trump Tower. Even Donald himself would approve.

Once you've figured out where you're staying, go out to the hundreds of Divvy bike racks scattered around town and rent a bike for $7 all day, which includes unlimited 30-minute rides. This is undoubtedly the best and only method of transport because it affords you the opportunity to soak in the views with minimal effort and a little breeze to cool you down during the burning summer months. Plan your trip accordingly by going to divvybikes.com and know where the stations are along your route so you don't need to go out of the way to return a bike. Armed with a way to get around, start your journey from the southern end of the Loop and move north, beginning at the best museum in a city packed with world-renown ones, the Field Museum. This is the home of the most complete T.Rex skeleton on the planet, Sue; it's so big the skull couldn't be mounted with the rest of the body due to its weight. Pay $18 for admission and spend 4+ hours learning about Egyptian tombs and human civilizations, then bike to the Shedd Aquarium next door. The price of admission is steep at $38, but Kristina and I had family connections that got us in for free. This is only worth visiting if you have children who love mischievous otters and prancing dolphins, but otherwise unremarkable, especially since we've visited the best aquarium in the world, the Georgia Aquarium in Atlanta. Now make your way north to Grant Park and Millennium Park along the Lakefront Trail, a bike trail running up the western edge of Lake Michigan, which appears so vast you'd mistaken it for an ocean. These open public spaces are some of the best we've seen in our travels around the country: they're lined with vibrant flora, beautifully manicured, and surrounded by the best skyline in the nation. In these parks you'll find the Buckingham Fountain (one of the biggest public fountains in the world making for a great photo-op), the "Bean" (properly named "Cloud Gate," a sculpture of highly polished stainless steel and the symbol of Chicago since 2006), the Crown Fountain (a person's face on a wall through which water pours from the mouth), the Jay Pritzker Pavilion (an engineering marvel with gorgeous design for aesthetics and acoustics), and the BP Pedestrian Bridge (a walkway passing over the road beneath for a great north to south view of the entire city). Continue your trek north along the Lakefront Trail to Navy Pier in the Streeterville district, the busiest attraction in the Midwest and the starting point of historic Route 66, which ends at the Santa Monica Pier in California. This dock extending into Lake Michigan is a conglomerate of shops, restaurants, and a Ferris Wheel all intended to reinvigorate your inner child with funnel cake and fried Oreos. Spend an hour before moving on to Lincoln Park a few miles north of downtown. This charming park includes a garden, conservatory, and zoo, all free and open year-round. Free parking is available on the side streets a couple blocks west. Walk around, interact with the lions and polar bears, then sniff some flowers for a few hours before heading to Big and Littles (1034 W. Belmont Ave) for a quick and cheap dinner. They serve the best truffle fries in town with some delicious tacos, but expect a long wait as they cater to hungry college kids. Then drive a short 5 minutes north to Chemically Imbalanced Comedy Club (1422 W. Irving Park Rd) for a taste of the famous improv scene only the Windy City can offer. Call it a night after a good laugh and a beer at the bar with fellow patrons and hear about how the locals live from the amicable bartender, Eric.

For your second day in the city, start the morning off right with a salivating brunch at Xoco (449 N. Clark St) in River North, the district across the river from downtown. Kristina and I have tasted churros from Barcelona to Miami--both with a prevalent Latino community--but the ones we ordered here in a town unknown for its Hispanic cuisine was honestly the best we've ever had. They also conjured up the best Mexican dish I've ever tasted, the pork belly chilaquiles, a crunchy mixture of tortillas, eggs, cheese, and savory pork. After a satisfying meal, make your way to the Loop and visit the Chicago Cultural Center. This is the venue the Mayor hosts dignitaries from around the globe and is home to the largest Tiffany-dome in the world. Quickly skim through the art expo there and find your way to the Michigan Ave Bridge about 5 minutes north. This pedestrian crossing takes you over the river into the Magnificent Mile, a mile-long road full of big chain shops and restaurants, Chicago's equivalent of Fifth Avenue in New York City. Immediately on your left are the Wrigley Towers, the headquarters of the chewing gum empire built in the 1920s, and on your right is the Tribune Tower, the home of the city's renown newspaper. Proceed northward along the avenue and end at the Hancock Tower, a spitting image of the tallest skyscraper in town, the Willis (previous Sears) Tower. Here, you can get the best panoramic of the city at the 360^o Chicago Observatory on the 94th floor. Or you can go to the SkyLounge restaurant or bar a floor below for the same amazing views for half the price if you order a drink or desserts to enjoy while peering down at the city. Just make sure to dress decently or the bouncers won't admit you.

For lunch, go to the nearby Gino's East (162 E. Superior St) for their famous original deep dish pizza. While Chi-town is known for the deep dish, locals swear they only eat thin crust, but if this is your first visit to the city, you can't leave without having tried this. Just order a small for 2 people and see what the fuss is about; the deep dish is overrated in my opinion, but a must-eat nonetheless. If you have time, go to Portillo's (100 W. Ontario St) also in the River North for another Windy City staple, the Chicago-style hotdog. Due to time constraints, Kristina and I were forced to try this at a food cart in the Museum District, but we heard Portillo's is the creme of the crop for dogs with a poppy seed bun, whole pickle, neon bright relish, and chopped onions. Remember not to commit the felony of using ketchup or the locals will make a scene. Also check out Do-Rite Donuts (50 W. Randolph St) near the Magnificent Mile or the original location in the Loop and get some pistachio lemon donuts for a sweet snack to power you through until dinner. After dinner, spend your night riding your bike along the lakeside and watch the weekend fireworks at the Navy Pier from the perfect vantage point on the trail. Walk towards the northern edge of the Loop and stroll leisurely on the Riverwalk, a pedestrian trail a level below the main streets of the city above, providing an awesome cityscape full of eclectic architecture towering overhead. Check-in to your hotel on the river and just marvel at the sights outside your window as you slip away from your busy day.

Chicago's local cuisine may be rivaled by New Orleans', its skyscrapers by New York City's, and its culture by San Francisco's, but spend a weekend exploring this town and it will capture your heart quicker than any other. The Second City has become our favorite American city, so come see for yourself why this little nook is the Midwest's best kept secret.

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Photos

Cloud Gate, AKA the "Bean"
The symbol of Chicago since 2006. Sculpted from 168 stainless steel plates polished seamlessly together.

Michigan Ave Bridge
Overpass looking down at the Riverwalk and architectural cruises.

Sue at the Field Museum
The most complete T.Rex skeleton in the world.

Buckingham Fountain
Located between Millennium and Grant Park; one of the largest public fountains in the world.

Chicago-style hotdog in the Museum District
Poppy seed bun, whole pickle, neon relish, chopped onions, and absolutely no ketchup.

The Ferris Wheel at the Navy Pier
The beginning/end of historic Route 66 and the busiest attraction in the Midwest.

Churros from Xoco in River North
The best Mexican cuisine in Chicago.

Chicago Cultural Center
Home to the largest Tiffany-dome roof in the world and venue for welcoming dignitaries.

Do-Rite Donuts
Try the pistachio lemon donuts.

Chicago skyline viewed from the Museum District
Outside the Shedd Aquarium in the South Loop.