Chicago is a big city, but it is absolutely possible to see all of the touristy sights in one day. I recommend starting reasonably early in the morning, 9:00 or 10:00, if you plan to spend a good bit of time in each location or if you are a “sight seeing walker”. If you are a fast walker and plan to snap just a few pictures, starting around noon will give you plenty of time.
I like to start in what Chicagoans call the “south loop” area. If you are taking the “L” (thats what the locals call the subway/city train system) hopping off at Jackson station on the Red Line and walking east toward Lake Michigan will take you to the start of the walking tour. (Check out a map of the Chicago “L” here.)
Grant Park/Buckingham Fountain
*Photo credit: Ally Heavens*
Starting in Grant Park, enjoy the open green park area where all kinds of local festivals take place throughout the year. Continuing through the east side of the park you’ll run into Buckingham Fountain. This fountain represents Lake Michigan, with four sets of sea horses symbolizing the four states, Illinois, Wisconsin, Michigan and Indiana that border the lake. Look to the north/north-west while you’re here and you will get a pretty great view of the Chicago skyline.
*PSA: If you are planning to do this on a Saturday or Sunday after 11:00 A.M., expect to be here for a few hours at the least. These are the most popular days and time to visit the Skydeck and lines will be VERY long.*
From Grant Park, make your way to Michigan ave then head west on Jackson Blvd toward the Willis Tower (you can call it the Sears tower if you want to feel like a local). If in need of a snack along the way, stop in to the famous Garrett’s Popcorn for a salty and/or sweet treat.
Adams Street/Beginning of Historic Route 66
From the glorious Willis tower, walk east down Historic Route 66. Yes, you read that right. The infamous Route 66 Starts in Chicago at Michigan Avenue. What is now called Adams Street, Route 66 would originally take you straight from Chicago, IL to Santa Monica, California.
Michigan Avenue, home to the “Magnificent Mile”, truly is magnificent. With enough shopping to put you in some serious debt and views you can’t find anywhere else in the world, Michigan ave does not disappoint. I have spent an entire day on Michigan ave alone and still not taken everything in.
First stop on Michigan Ave will be Millennium Park. Here you’ll see the infamous mirrored “Bean” or Cloud gate, Lurie Garden, and the Jay Pritzker Pavilion.
Millenium park is home to many summer concerts and small festivals throughout the year. In the winter, two ice rinks are placed in this park. One is a simple, oval shaped rink on the west side of the park situated beneath the Cloud Gate and the second is on the east side, in Maggie Daily Park, in the shape of a skate ribbon.
The Cloud Gate /“Bean”
You don’t think “Chicago” without thinking, “giant mirror thing in the shape of a bean”. So, here she sits, in all her mirrored glory. Release your inner child here. Take pictures of the skyline from all angles, take mirror selfies, make funny faces at yourself and others and run underneath and oggle at the kaleidoscope effect. For such a simple piece of art, it can entertain for quite a long amount of time.
Time for a breather. Grab a pretzel or hot dog from a vendor and stroll through the garden or sit on a garden bench and forget that you’re in an insanely busy city for a minute.
Jay Pritzker Pavilion
If you’re visiting in the Summer months, you may get lucky and happen upon a free concert, part of the Grant Park Music Festival, being held at the Pavilion. The Grant Park Music Festival is an annual, ten week classical music concert series held in Chicago, IL. It features the Grant Park Symphony Orchestra and Grant Park Chorus and other featured guest performers and conductors.
If you’re not visiting in the Summer months, it still makes for some really pretty photos.
The Chicago Theatre
From Grant Park head west back toward Michigan ave, walk north to Randolph street, and walk west for a couple of blocks until you reach State Street. Look right (north) and you will have “CHICAGO” staring back at you. Are you really in Chicago if you don’t prove it by taking a picture in front of the infamous “CHICAGO THEATRE” sign?
City Winery & Frost Gelato on the Riverwalk
Walk north on State Street and enter the Riverwalk on the corner of State and Wabash. At the bottom of the stairs, you will find the City Winery and Frost Gelato and a relaxing view of the river. During the summer it is packed, but people are friendly and will make room for newcomers.
Walk along the riverwalk and take in the serene waterfront stroll. Wave to the passing boaters, look up and see just how tall all the surrounding buildings are, this isn’t normally on a travel guide to Chicago but I think its an absolute must.
Michigan Ave/DuSable Bridge
Along the riverwalk, you’ll reach Michigan Avenue once again. Head up the stairs to continue the walk along the Magnificent Mile. On the Michigan Ave/DuSable Bridge, you’ll, find one of my favorite views of the city. To the east, you’ll see the river running out to Lake Michigan lined by buildings of all sizes. To the west, you’ll see the the tallest buildings lining the river and, if caught at the right time of day, a magnificent view of the sunset over the river and city.
The Wrigley Building
At the north end of the Michigan Ave bridge, you’ll find my favorite building in the city of Chicago, The Wrigley Building. With its white stone walls, intricate decor and gold accents, you can’t help but fall in love with this building.
The Magnificent Mile (Michigan Ave)
Here begins the shopping portion of the Magnificent mile. If you are hoping to go on a shopping spree, continue on right along on Michigan ave, if not, walk a short way, take in the glorious sights and plan to head to the next destination.
Walking north on Michigan Ave, find E Illinois Street and head east toward The Navy Pier. Here is a good place to get dinner with so many restaurant options available. Harry Caray’s tavern is one of my favorites.
Take a spin on the Centennial Wheel, Chicago’s Ferris wheel, for a fantastic view of the city and a fun way to begin finalizing what has been a long day of walking around. Enjoy another view of the skyline and watch the boats come in and out of port as you walk toward the tip of the pier. At the end of the pier, take in just how great of a “Great Lake”, Lake Michigan is.
Finish Mag Mile
If you’re not already exhausted with throbbing feet, continue back down E Illinois Street toward Michigan Ave and finish up the Magnificent Mile by walking north to the end of the road. Stop in some shops if there’s time, take some pictures in front of things you couldn’t afford in your dizziest daydreams, grab a treat in one of the many sweet shops and cafes along the way or just simply walk and take in all the city lights.
John Hancock Observatory at End
If your up for another stunning, high up view of the city, head in to John Hancock Tower. Here, there is an observatory called “360 Chicago” & “The Tilt”, or head to the “Signature Room” on the 95th floor for a night cap and a beautiful view of the city.
Wow, that was a long day. I hope you enjoy the great city of Chicago. If you have ever visited, or visit and this post helped to give you some guidance, I’d love to hear all about it! Happy traveling!
*All opinions are my own. All photos are my own unless stated otherwise (credit given beneath photo). This post is not sponsored. I do not receive compensation for any links followed and/or products purchased from links attached*