Ultimate Guide to Chicago

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When to Visit?

Enjoy Chicago to the fullest in the warmer months. Late May to Mid-September will get you the best weather. And I say this because it is my favorite time to be here.

March to May: Weather will be volatile and unpredictable during this season.  The days can go from freezing cold to tolerable 50s. It’s still considered the low season, so it won’t be too crowded.

June to September: This is the best time to visit. Most likely perfect weather, warm long days and sunshine, with the occasional rainy day.

October to November: If you enjoy the change in seasons then visit during this time. The winds will still be mild and the occasional changing leaf here and there.

December to February: Just make sure you bundle up. December is tolerable due to the Christmas jolly atmosphere. The following months will be freezing, snow storms, strong winds. Nothing layers, layers and more layers can’t help. Warm coat, scarf, hat and gloves are necessary for survival.

How to Get Around?

Chicago has a great transportation system. The “L” offers 7 train lines that run across the city, 2 that go to the airports, and the best part is, they all “Loop” around downtown. The bus is also very reliable if you want to travel shorter distances within the major sites. Visit the CTA site for more information. For convenience seekers, Lyft and Uber are also a popular form of transportation.

What to See?

Willis Tower Skydeck

233 S Wacker Dr, Chicago, IL 60606

How would you like to step on the ledge and stand at 1,353 feet in the air, 103 stories high to be exact? This is an obvious choice when visiting Chicago. The view is worth it. Plan your skydeck visit to one of the tallest buildings in North America.

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Sky Deck at night

Millenium Park

201 E Randolph St, Chicago, IL 60602

Since the opening over a decade ago, Millennium park has increased in popularity making it the top of the list in most Chicago itineraries. Visitors love to visit Cloud Gate, splash around in Crown Fountain and attend all the free events and concerts at J Pritzker Pavilion such as my ultimate favorite, Summer Film Festival.

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Crown Fountain

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Cloud Gate “The Bean”

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Jay Pritzker Pavilion

Museum Campus & Soldier Field

Museum Campus is along Lake Michigan and it’s home to Soldier Field, Shedd Aquarium, Field Museum and Adler Planetarium.

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View from Museum Campus

Want to look at the stars and learn about the planets? Adler Planetarium has featured shows, exhibitions, and events. And if looking for something more adult, enjoy Adler After Dark. A private event for those over 21 the theme changes every time.  For a list of what is included check out Adler After Dark.

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Adler Planetarium

Field Museum houses 30 million objects and specimens, geological, biological and cultural objects. Learn more about the temporary exhibits and events happening at the museum. At FieldMuseum.org you will find tickets and information.

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Field Museum

Shedd Aquarium is home to 32,000 aquatic animals and one of the largest indoor aquariums in the world. Plan your visit to Shedd Aquarium and enjoy from Caribbean Reef, Wild Reef, Abbott Oceanarium and many more.

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Magnificent Mile

The Mag Mile is the best place to shop until you drop. With hundreds of retailers to pick from and the best flagship stores. Shopping Michigan Avenue can turn into an all day event. Shop the Water Tower Place, The Shops at North Bridge, 900 North Michigan Shops, Apple, Nike, and many others.

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View of Water Tower Mall and John Hancock building

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View of Michigan Avenue

The Art Institute of Chicago

111 S Michigan Ave, Chicago, IL 60603

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Ranking at the top of TripAdvisor for some of the best Museum’s in the world, the Art Institute is a must see. Click here for tickets and information. Art works ranging from the Impressionists, Reinaisance, ancient artifacts and abstract works on the modern wing.

Museum of Contemporary Art

220 E Chicago Ave, Chicago, IL 60611

Love contemporary art? Their aim is to bring the public to experience the work and ideas of living artists. Enjoy the surrealism, sculptures, installations and many more. Check out MCA.org for tickets and a list of current exhibitions.

Architectural Boat Tour & River Walk

Chicago has a rich architectural history. What a best way to see it than on a boat along the Chicago River. It is a tradition of mine to always get on a boat in every city I travel to, so of course when it comes to my beautiful city, I absolutely recommend it. Visit Shoreline Sightseeing to look at tickets and tours available.

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If boats are not your thing, just take a walk along the river… and enjoy the view.

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Navy Pier

Navy Pier is the #1 Leisure Destination in the Midwest, it welcomes millions of visitors annually. In 2016 Navy Pier will celebrate its 100th anniversary.

The attractions Include:

  • Centennial Wheel
  • IMAX Theatre
  • Shakespeare Theatre
  • Cruises
  • Shops

For a complete list visit here.

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The New Centennial Wheel Opens May 27th

Wrigley Field

Chicagoans love their sports and are very loyal to their teams. This iconic ball park is as chicagoan as it gets. Get some tickets, and go to the ball game. There are many bars in the surrounding are as well as rooftops to watch the game from. Purchase Cubs tickets here.

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Lincoln Park Zoo

Lincoln Park Zoo is a family favorite, not only is it free, but is a decent size and won’t get the kids too tired. Enjoy visiting the Lion House, Primate House, African Journey and many others. LP Zoo is also a short distance from Lake Michigan. Plan your visit here.

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I named him, Richard Parker, in honor of one of my favorite movies, Life of Pi

John Hancock Center

I’m letting you in a little secret, the view from the 96th floor of the signature lounge is the best in the city, particularly from the ladies restroom. Don’t leave Chicago without enjoying a cocktail with a view.

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Second City & Stand up Comedy

Some of the best Stand Up Comedians came out of Chicago. Do the names Rachel Dratch, Tina Fey, Tim Meadows, Mike Myers, and Bill Murray sound familiar? They all performed at Second City. It’s fair to say Chicago has great stand up comedians.

Broadway in Chicago & Off Broadway

Chicago doesn’t take a back seat to Broadway in NYC. Broadway in Chicago puts up a good fight. The cities’ talented actors not only reside on Broadway, there are numerous theaters throughout the city.

Broadway

  • The Book of Mormon
  • The SpongeBob Musical
  • The Sound of Music
  • Beauty and the Beast

Click here for tickets and information.

Off Broadway theatre is always changing and the theaters represent each Chicago neighborhood, click here for a complete list of shows.

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Grant Park

337 E. Randolph St. Chicago, Illinois 60601

A 319 acre public park in the heart of the business district. It is the center piece of the city. The highlights are: Buckingham Fountain, Tiffany Garden, Millennium Park and Maggie Daley Park.

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Buckingham Fountain

Walking Architecture Tour

Whether you book a walking tour with the Chicago Architecture Foundation or create your own. Walking down the loop is a feast for architecture fanatics, so put on your walking shoes and scout the streets of the loop in search of Chicago windows, clocks, and so much more.

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Music Festivals

No Guide would be complete without music.

Chicago has been home to Lollapalooza for 25 years. This year it will celebrate its 25th anniversary with a four-day event. For tickets and line up visit Lollapalooza.

Pitchfork is a summer music festival held in Union Park. For the line up and ticket information visit Pitchfork Music Festival.

Chicago Eats

Deep Dish Pizza

  • Gino’s East
  • Giordano’s
  • Pizzeria Uno

Italian Beef

  • Al’s Beef
  • Portillos

Chicago Dog

  • Weiner Circle
  • Superdawg
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Wiener Circle

Kayak the Chicago River

This tour is out of the box and worth trying, Kayak Chicago offers a variety of tours, Fireworks paddle, Lake paddle, Architectural tour, Sunset paddle and a few others.

Check out:

Kayak Chicago

Urban Kayaks 

Lake Michigan

Chicago has 26 miles of public beaches, and the beach season opens on May 27, 2016.

Find the complete list at ChicagoBeaches, some popular beaches are:

  • North Avenue Beach
  • Oak Street Beach
  • Montrose Beach
  • Ohio Street Beach

Neighborhood Fests

  • Roscoe Village Burger Fest
  • Wicker Park Fest
  • Taste of River North
  • Fiesta del Sol
  • Lincoln Park Greek Fest

For a complete list visit: cityofchicago.org

United Center

Home of the Chicago Bulls and Blackhawks, United Center is a city staple. If you ever find yourself in the city during the season, don’t miss out attending a game.

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Venture Out

Brookfield Zoo

Fashion Outlets

Evanston

Scenic Drive on Lakeshore Drive

I hope you enjoy your visit and find this guide helpful.

-Mayra

 

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