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.
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.
Museum Campus & Soldier Field
Museum Campus is along Lake Michigan and it’s home to Soldier Field, Shedd Aquarium, Field Museum and Adler Planetarium.
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.
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.
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.
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.
The Art Institute of Chicago
111 S Michigan Ave, Chicago, IL 60603
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.
If boats are not your thing, just take a walk along the river… and enjoy the view.
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
For a complete list visit here.
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.
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.
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.
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.
1616 N Wells St, Chicago, IL 60614
1548 N Wells St, Chicago, IL 60610
230 W North Ave, Chicago, IL 60614
1531 N Wells St #5, Chicago, IL 60610
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.
- 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.
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.
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.
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.
Deep Dish Pizza
- Gino’s East
- Pizzeria Uno
- Al’s Beef
- Weiner 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.
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
- 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
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.
Scenic Drive on Lakeshore Drive
I hope you enjoy your visit and find this guide helpful.