My adventure has finally begun and I’m in the Windy City! I am so happy to kick-start my travels here and offer you an insider’s guide to Chicago, one of my favorite places on earth. I first fell in love with the Windy City the summer of my 15th birthday. The fireworks over Lake Michigan, lively sidewalk cafes, and warm summer air captured my heart. I was spellbound. Three years later I moved to Chicago where I lived during the four years I attended University. One of the reasons I feel so at home in the city is because of the friendliness of the people who live here. Chicago has all of the perks of big city life- world famous culinary delights, nightlife that never sleeps,  fantastic artwork, and beautiful public parks. Yet, I find it’s not overwhelming like New York can be, or sprawled out like Los Angelos. There is a grounded, small town feel here that I love. Even though I no longer live here I still visit often and find reasons to keep coming back. Here are a few of my favorite things to do in Chicago along with some general tips on how to best enjoy the “Second City.”

Transportation/Accommodation
       The best time to visit Chi-town is hands down during the months of May-September. Summer in the city is the best time to take advantage of festival season and enjoy some time on the beach. The months of October-April can be bitterly cold and yes, wind.
      Public transportation is fairly dependable and you can get anywhere in the city this way. Both of the two main airports are accessible by train (the “L”) which is the best way to get around. If you’re staying for more than a few days, buy a Chicago CTA pass which will give you discounted prices on bus and subway fare. If you’re staying for a week, the 7 day pass is $28, otherwise it is $2.50 each way for buses and trains.
The grid-system is very easy to navigate by foot and a nice way to see the sights in warmer weather. Biking in the city can be nerve wrecking, but most streets have bike lanes. Parking is a nightmare in Chicago and best to be avoid no matter where you’re staying.
      There are several hostels to choose from (I’ve stayed in the Getaway Hostel before), but make sure you ask how close they are to public transportation. Most hotels will be around $150 and up per night unless they are in the outskirts of the city. One hotel I would highly recommend is the Holiday Inn at Chicago Mart Plaza.* This hotel is located downtown overlooking the Chicago River. Most rooms have a panoramic view of the city skyline, and their Cityscape bar offers a delightful view as well. There is an indoor swimming pool, fitness center, and restaurant. The Brown Line subway is located within a few blocks of the hotel making it convenient to explore the city. Rates for two adults start at $75.00 per night (weekend rate, AAA discount applied). I’ve personally stayed at this hotel and was very impressed with the service and accommodation. For the price and convenient location, it can’t be beat! Of course, couch surfing is another option for a wallet conscious traveler hoping to interact with the locals!

Top 10 Things To Do 
1) Stare at the penguins and giraffes at the free Lincoln Park Zoo and then visit the neighboring (also free) Chicago Botanic Garden.
 2) Catch a view of the city at night from the 95th floor of the John Hancock tower while enjoying a cocktail at the Signature Room.
3) Every team can have a bad century, right? Don’t miss seeing the endeared Chicago Cubs play a baseball game at Wrigley Field.
4) Walk around the Old Town neighborhood and then catch a stand-up act at Second City, once home to famous SNL alums.
5) Eat a slice (or two or three) of Chicago style pizza at Giordano’s, my favorite pizza joint.
6) Walk around Millennium Park and take a self portrait in reflective Bean (also known as “Cloud Gate.”)
7) “On State Street, that great street, I just want to say, they do things that they don’t do on Broadway.” (Frank Sinatra) Head to the Theater District and enjoy some window shopping on State Street.
8) Al Capone is not the only sketchy part of Chicago’s history. Learn about the dark side of the Windy City by taking a Gangster’s and Ghosts bus tour through the city.
9) Take the Red Line to Chicago’s China Town and sample some of the homemade goodies at one of the Chinese bakeries or buy a surprise souvenir for a dollar.
10) Visit the impressive Chicago Art Institute and stare at some of my favorite pieces of work from Picasso and Degas.

Tourist Traps to Avoid
     Navy Pier is one of the most overrated attractions in Chicago. Located on the old naval pier, in a generic shopping center it has an Imax theater, restaurants, and a Ferris wheel, however it is overpriced and designed to take your money. Michigan Avenue is also known as “Magnificent Mile” and has many high end stores, however it can be crowded and touristy, similar to Times Square. The Sears Tower is a famous building in the Chicago skyline, however it’s not necessary to pay for a ticket to the top. Go to the John Hancock building instead. Blue Man Group is a variety show with a huge reputation in Chicago, however for the price the entertainment is overblown. See a show at Second City instead.

Other Resources
     “Kiss and ride on the CTA” Plan your trip around the city using public transportation with the Chicago Transit Authority website. You can also download a bus tracker app to your phone so you can reduce the time spent waiting around in the cold for the bus to arrive!
    The Chicago Reader is a free magazine that publishes the scoop on local events and venues around the city. It also features articles on current news, and an adorable Matches section called, “I Saw You” which I can’t help perusing every time.
    The Red Eye is another free publication with current news and events.
    The Chicago Public Parks District often has free events at many parks throughout the year. Check here for an updated list of events.

*This is not a sponsored post. All opinions are my own, based on personal experience. Photos are taken by me.

Have you visited the Windy City? Would you like to in the future? Leave a comment below with your thoughts!