Chicago trip highlights Part 1: What to do in Chicago

Over the July long weekend, my boyfriend and I set off on a road trip from Toronto to Chicago.  With excited anticipation we packed up the car, rolled the windows down and drove off as the sun rose on a new adventure!  8 hours later we arrived in Chi-town for 3 days of sightseeing and exploring.

And boy was it HOT!! With temperatures in Chicago ranging from 96-100 degrees Fahrenheit we covered a lot of ground walking everywhere (this is one of my favourite ways to explore even though it leaves my feet sore).  Over 3 days we…filled our tummies with deep dish, braved a boat ride on Lake Michigan during a sudden dark storm, experienced wicked blues music and toured the famous Wrigley Field.

Chicago is a very historic city.  It rebuilt itself after surviving a devastating fire in 1871 that destroyed 3.3 square miles of the city, it is the birthplace of the skyscraper, America’s architectural capital and is well known for its music scene.

This was my first time in Chicago.  I found the longer I stayed, the more the city grew on me.  What is wonderful about this Chicago, and unique to the other cities I have been to, is that you can take in the excitement of the downtown of a large city while at the same time having multiple usable beaches so close and accessible to the downtown core.  I discovered there is a lot of Chicago to see and of course, over 3 days, it was not possible to get to it all.

Here are some of my trip highlights:

1.       Walking the streets and exploring Chicago neighbourhoods:

North Michigan Avenue (aka the Magnificent Mile) and State Street

Tall buildings and doors of department stores and fashion retailers line these streets tempting you with their large window displays and sale signs.  There is plenty of hustle and bustle here as per usual downtown city cores.  You could easily spend a day going from store to store and leaving with your hands full of shopping bags.  These streets are home to such stores as Nordstrom, Macy’s, H&M, the Gap, Hermes and Coach.  Walk South down the Magnificent Mile to take in the view of the Chicago River and look up to gaze at the surrounding architecture.

Gold Coast

North of the downtown core, I found this neighbourhood to be more residential, trendy, charming and quieter then the downtown area.  This is a nice area to slowly walk through and explore.

“The Bean” – Millennium Park

This elliptical outdoor sculpture made of steel is a VERY popular tourist attraction (notice the mass gathered around “The Bean”) and for good reason.  Polished to a high shine, this bean shaped sculpture gives a perfect reflection of the city skyline and anyone surrounding it.  It is a really cool piece of public art, however it can be very difficult to find an open spot to snap a photo without anyone in it. Be sure to get there before the park closes at 11pm.  I learned the hard way when going back to try and snap a night time photo.

2.        Chicago River Boat Cruise:

The Chicago River snakes through Chicago. Lined with the skyscrapers that draw your eyes upwards the river sparkles and glistens under the sun.  You can walk along the river, which is beautiful and picturesque in itself, but a great way to see the river and the surrounding architecture is through a River Boat Cruise.  There are many tour operators waiting to take tourists aboard.  There are 2 route options available, one which takes you to 2 parts of the river and onto Lake Michigan for a view of the city skyline from the lake and one which takes you to all 3 river branches.   We chose Mercury Cruiseline for a 90 minute boat ride ($28/person – $25 if you purchase them online in advance) through the river and onto Lake Michigan.  The cruise is narrated by a tour guide who takes you back in time with details about the history of Chicago and its architecture, all while gliding along the Chicago River and Lake Michigan.

Upon entering Lake Michigan, a sudden storm came out of nowhere!  One minute it was balmy and sunny, the next large dark menacing clouds cloaked the sky.  Thankfully we never felt unsafe on the boat, the worst that happened was that we got wet.  We were still able to get a great view of the Chicago skyline and take these photos…

This is a moment for the memory books!

A very popular attraction is the Architecture Foundation River Cruise by Chicago’s “First Lady” which takes passengers through all 3 branches of the river and goes into greater detail about the buildings that create the story of Chicago ($38/person – $35 if purchased online in advance).

Most tour operators can be found along Michigan Avenue and Wacker Drive.

3.        The Waterfront and Beaches

The Waterfront

Chicago sits on Lake Michigan.  Taking advantage of this, the city created a beautiful waterfront area for Chicagoans to enjoy.  Lake Shore Drive is made up of a long path following the waterfront making for a peaceful and scenic promenade for walkers, joggers and bikers.  Follow the path and pass by harbours full of sailboats.

Navy Pier

Navy Pier was very busy on the weekend!  Full of tourists, young and old, the pier was pumping music and packed with people walking along, enjoying drinks on patios, savouring yummy ice cream treats, riding the Ferris wheel and taking in a game of mini golf.  The Ferris wheel stands at 150 feet high and is a replica of the very first Ferris wheel which was built in 1893 for Chicago’s World’s Columbian Exposition.  You can take the 7 minute ride for $6 per person and the view is incredible!

View from the top of the Ferris wheel

Sun sets on Chicago city skyline – behind Navy Pier


Ohio Street Beach – small beach just a short walk from our hotel

My favourite part about the waterfront was the beaches!  To my surprise, Chicago has multiple clean sandy beaches on Lake Michigan, perfect for a refreshing dip to cool off on a hot summer day! How awesome is it that this exists in a major city just steps from downtown?  A nice reprieve from busy, noisy streets!  North Avenue Beach is a clean, wide and long stretch of golden sand complete with over 50 volleyball nets, food vendors and a shallow shore wonderful for just dipping your feet in, wading in for a swim and for families young ones to swim in.  This beach also offers a nice view of the city skyline!

North Avenue Beach

Check back for Part 2…more highlights include deep dish pizza, tour of the historic Wrigley Field (home of the Chicago Cubs) and hitting up a blues bar!

For more photos from my trip, see my Chicago album on Flickr.

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3 Responses to Chicago trip highlights Part 1: What to do in Chicago

  1. Oster's Mom says:

    You are definitely in a great city!

  2. Joyful says:

    Thanks for sharing your Chicago moments…good info and some fabulous pictures!!

  3. Pingback: The 15 Worst Airports in America Right Now | Blog

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