Winter in Chicago

Winter in Chicago

Alexis Garhammer
Things to do when it’s best to stay inside
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Areas & Neighborhoods

Museum Campus

Museum Campus is a 57-acre park in Chicago facing Lake Michigan in Grant Park. It encompasses five of the city's major attractions: the Adler Planetarium, America's first planetarium; the Shedd Aquarium; the Field Museum of Natural History. This is also where Soldier Field is located.

Millenium Park

The lakefront campus, located in the heart of downtown, is home to the iconic Cloud Gate statue (aka “The Bean”), interactive fountains, tranquil gardens, free events, public art, skating rinks, rock climbing, and plenty of green space.

Michigan Avenue

You’ll be on this street for most of your time in the city. The Art Institute, Millenium Park, and shopping are located along this street. Also known as the Magnificent Mile.

State Street

Runs parallel to Michigan Ave. Also known for shopping. The Chicago Theater is on State Street.

Northside

Lakeview, Wrigleyville, Lincoln Park, Andersonville. Where people root for The Cubs

Southside

Where people root for The Sox.

Wrigleyville, Lincoln Park & Lakeview

Neighborhoods north of downtown. Also where Boystown is located - the gay neighborhood in Chicago. Great areas for drinking and bars. Wrigleyville is where Wrigley Field is. Go Cubs.

Pilsen

Come for the Mexican food. This is known as the Latino neighborhood.

Orange Line

Train to Midway airport.

Blue Line

Train to O’Hare airport and Wicker Park/Bucktown.

West Loop

Hip neighborhood that was formerly an industrial area. It’s where “restaurant row” is located and lots of nightlife. A little bland in terms diversity and architecture, but a great area to come eat and get schwasted. Where rich tech kids buy condo’s.

Wicker Park/Bucktown

This was known as the hipster neighborhood (when I lived there 10 years ago). “Artsy at heart” with lots of music venues and vintage stores.

The Viagra Triangle

Known as the Viagra Triangle - you’ll find rich old men taking out younger women. Known for nightlife and bars.

Do’s

Dress for bone-chilling cold

Wear shoes that are warm and okay to get wet.

Make reservations in advance

For the fancier restaurants and bars.

Ride the CTA

It’s easy and part of the fun. CTA = Chicago Transit Authority. Includes the train and the bus. The different train lines are colors (orange line, blue line, red line). The “loop” is the center of Chicago and taking the above ground train around the loop is a great way to see the city.

Watch Ferris Bueller’s Day Off

And then wish you were there in the Summer. It’s okay - you can come back.

Don’t’s

Order a hot dog with ketchup

Just don’t.

End up on Lower Wacker

Wacker Drive is a street that runs along the Chicago River. There is an Upper Wacker and Lower Wacker. It’s not necessarily unsafe on Lower Wacker, it’s just very easy to get lost. If you end up down there, just find the next set of stairs to get back to Upper Wacker. Fun fact - scenes from Batman The Dark Knight were filmed on Lower Wacker.

Stay only on Michigan Ave

The neighborhoods are not hard to get to - and the best bars and restaurants are NOT on Michigan Avenue.

Pronounce Wabash Avenue wrong

It’s WAbash, not waBASH. You’re welcome.

Forget Souvenirs

Garrett Popcorn Shops
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Mix of caramel and cheese. There is one at Midway Airport to get as you leave. Get a bag for the plane.
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Activities

When you are not eating.

Architecture Tour

The boat tour is the best thing to do in the summer, but this is the winter alternative. This is also a friendly solo activity. Highly recommend any architecture tour. You can also do a tour by the “L train” (short for elevated train)

The Second City
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Famous comedy club. Buy tickets in advance. The Second City alumni include, Bill Murray, Gilda Radner, John Candy, John Belushi, Dan Aykroyd, Eugene Levy, Catherine O'Hara, Chris Farley, Tim Meadows, Mike Myers, Steve Carell, Jordan Peele, Tina Fey, Amy Poehler, Stephen Colbert, Cecily Strong, and Aidy Bryant.
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The Art Institute of Chicago
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One of the best (the best?) art museums in the country. Have an existential crisis while staring at the Seurat like Cameron in Ferris Bueller’s Day Off.
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Cloud Gate
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Located within Millenium Park. Grab a coffee from Intelligentsia on the other side of Michigan Ave and stroll through the park. Come photo ready for selfies at the bean.
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Shedd Aquarium
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Field Museum
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Natural history museum located on Museum Campus.
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Museum of Science and Industry, Chicago
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This is one museum that is further out from downtown, but super fun.
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The Chicago Theatre
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Check if there are any shows in town.
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See The Blackhawks or The Bulls

You know, Michael Jordan.

Do a Brewery Tour

Technically this does fall under the eating and drinking category. So sue me. Chicago has an epic midwestern beer culture. You can do a brewery tour at any of the following.

Goose Island Taproom
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Revolution Brewing - Brewery & Taproom
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Half Acre Beer Co
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Bars & Casual Food

875 North Michigan Avenue
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There are two tall buildings that you can pay to go up and see the view. The Willis Tower (formerly the Sear’s Tower) is the most famous, or the John Hancock Building, which is located on Michigan Avenue. My tip: take the elevator up to the Signature Room on the 95th Floor at the John Hancock and get a drink with a view instead of paying to go to the observatory. Perfect after shopping and to warm up with a hot cocoa or coffee.
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Portillo's & Barnelli's Chicago
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There are multiple Portillo’s locations, but this is “the one”. Any location will suffice. The order: Chicago dog, Italian beef, fries and a chocolate cake shake. Let the grease and happiness wash over you.
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Carnitas Uruapan
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Carnitas. By. The. Pound.
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The Game Room
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Located within the Chicago Athletic Association hotel, this is a great place to hang in doors grab drinks and play games. Daytime or evening.
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The Green Mill
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Prohibition era jazz bar frequented by Al Capone. Open late.
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Time Out Market Chicago
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One of those dining hall concepts. I’ve never been here but if you can’t decide where to go this would be a good spot. Located in the West Loop.
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Lou Malnati's Pizzeria
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If you have deep dish, this is the one I would recommend. There are multiple locations but this one is closest to your hotel.
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Lost Larson (Andersonville)
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Take the bus to Andersonville, a neighborhood north of Wrigleyville for pastries that will make you cry.
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Reservations Required

The Aviary
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Famously bougie bar that requires reservations. Inventive fun cocktails.
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The Violet Hour
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Alternative to The Aviary. Speakeasy bar with fancy cocktails.
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Girl & The Goat
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From Stephanie Izard of Top Chef. She has multiple restaurants in Chicago and all of them are well known staples.
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The Publican
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Beer, meat and vibes.
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Cindy's Rooftop
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Make a reservation!! This is a great “first night” place to go. Not too fancy but hard to get reservation at the top of the Chicago Athletic Assocation hotel. Beautiful views over Millenium Park.
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Gibsons Bar & Steakhouse
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Located in the Viagra Triangle. Traditional Chicago Steakhouse.
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Little Goat Diner
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Another Stephanie Izard.
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Au Cheval
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The Burger.
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Vibes

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