Chicago night skyline across Lake Michigan

Situated in the Midwest along the Great Lakes shoreline, Chicago is the third largest city in the US (by population). Known for its restaurants, parks, shopping, culture and, of course, Lake Michigan, Chicago is the perfect place to visit for a weekend break or longer. Here's some insider info from a local to help you plan your trip.

Trains passing over the tracks in downtown Chicago

Chicago has one of the best public transportation systems in the U.S.

Paris has the Métro, London has the tube, and Chicago has the L. The CTA (Chicago Transport Authority) is the nation’s second largest public transportation system and it operates both the train and the bus lines. The Chicago elevated (L) train system is affordable, expansive and easy to navigate, connecting both airports to downtown and the surrounding suburbs.

It won’t take long to get the hang of which train will take you where you want to go since the lines are designated by specific color (blue to O’hare, orange to Midway, red to go to the Magnificent Mile, green or pink for the West Loop). You can follow directions on Apple Maps, Google Maps, or download the Transit Stop: CTA Tracker app.

Chicago skyline with skyscrapers viewed from Lincoln Park over lake.

Chicago is on a Great Lake

Chicago is located on Lake Michigan, one of the five Great Lakes in the U.S., and the largest lake (by area) to exist in one country. If you’ve never seen a Great Lake, imagine a freshwater ocean without sharks. And Chicagoans love ‘the lake’!

Running along the lakefront is The Chicago Lakefront Trail, an 18 mile shared pedestrian and bicycle path which passes in front of numerous beaches and restaurants.

The patio of Lark restaurant in Chicago

Chicago is a city for food lovers

Go to any major publications list of best restaurant city and Chicago is bound to be near the top. Of course it has it’s fair share of Michelin-starred restaurants, but the real draw is that you can get almost any cuisine you are looking for at a (relatively) affordable price. Even better it comes without a pretentious undertone, while sitting in either a beautiful restaurant or one of the many outdoor patios Chicago is known for. Because locals love their restaurants, it’s always best to make a reservation!

The famous signage on a warm summer's night at Wrigley Field

Chicago is not a town of fair-weather fans

The sports fans in the city are ferociously loyal to their teams. It’s no wonder since all of the major sports (football, soccer, baseball, basketball and ice hockey) arenas are located in city-proper. It doesn’t matter the season, chances are if you find a local they (or someone they know) have plans to root on their favorite team in person.

If you visit in the summer the red line (see above re: public transportation) can take you directly to see the Cubs play at Wrigley Field or the White Sox play at Guaranteed Rate Field.

Chicago Oak Street Beach

The best time to visit Chicago is in the summer

Since it’s located in the upper midwestern portion of the U.S, it’s no surprise that winter can be fierce in Chicago, with blizzards and negative degree temperatures not uncommon. While locals make the best of winter with ice skating in Maggie Daley Park and getting bundled up to root on the Bears, real Chicagoans appreciate summer because the winters are so harsh.

Summer in the city is for patio cocktails, dining al fresco, walking the lakeshore, catching a baseball game, having a picnic in a park, getting some vitamin D at the beach, visiting the animals at the free Lincoln Park Zoo. Check out this three-day Summer itinerary to take the planning out of your next trip. The days are long and the weather’s mild which makes for the perfect season in Chicago.

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Jessica Lee

Author - Jessica Lee

Jessica Lee is the founder of Very Obsessed, a travel, lifestyle, & entertainment blog for the modern Xennial. When she's not chilling at home in Chicago with her blind cat, you can find her exploring a new city or bingeing a new show, ideally en route.

Last Updated September 6, 2021

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