A perfect day in Chicago, the Windy City

Chicago has been inspiring architects, writers, celebrities, locals and tourists since decades. The Windy City rose from its own ashes, like the mythical phoenix, after the Great Chicago Fire and continues to soar into the sky even today. Frank Lloyd Wright, the great architect, said of Chicago “Eventually, I think Chicago will be the most beautiful great city left in the world.” Mark Twain, the famous writer described the city as “She is novelty; for she is never the Chicago you saw when you passed through the last time.” And Oprah, who can think of Chicago without Oprah, said “My first day in Chicago, September 4, 1983. I set foot in this city, and just walking down the street, it was like roots, like the motherland. I knew I belonged here.” For me, Chicago was the first US city I ever saw, Chicago was the first US city I called home. I have lived in the glorious Downtown and walked daily past the Willis Tower on my way to grad school. I have lived in the suburbs and experienced Chicago’s great public transportation. I have experienced the City’s harsh winters and lived through the terrible Groundhog Day Blizzard of 2011 which dumped 21.2 inches of snow on the city. I have seen the city and its people come alive in summer. I love Chicago and proudly wear my heart on my sleeve. This is my take on spending a perfect day in this beautiful city.

The best time to visit Chicago is in summer when a multitude of events take place in the city, variety of temporary public art springs up throughout Downtown, music booms through the city’s sidewalk cafes and restaurant patios, a fleet of cruise ships dots the Chicago River and Lake Michigan and both the sky and the Lake are cornflower blue. The best way to commute in Chicago is by walking; you get a firsthand look at the finest architecture in the country and can click photos whenever you see something you fancy. The other convenient ways to see Chicago include taking the ‘L’ trains and buses, and the water taxis. Stay in a hotel in the Loop or in the Magnificent Mile area and explore the sights this beautiful city has to offer.

In the morning: Take a gravity defying photo on the Skydeck Ledge at Willis Tower

Willis Tower is the tallest building in Chicago and 2nd tallest in the country

Willis Tower, with its 108 floors, is Chicago’s tallest building and Skydeck, the building’s observation deck, is located on its 103rd floor. The Skydeck Ledge is a set of all-glass balconies that extend from the façade and allow visitors to look through the glass floors to the streets below. Standing on the Ledge and seeing the city go about its day thousands of feet below is a thrilling experience. Taking incredible photos on the Ledge is one of most popular things to do in Chicago.
Willis Tower is located at 223 S Wacker Dr

Skydeck Ledge is a set of all-glass balconies that extend from the façade and allow visitors to look through the glass floors to the streets below

Travel Tip: I recommend starting your first day in Chicago by visiting the Willis Tower in the morning. In an ideal world, the Willis Tower always has perfect visibility and no crowds. However in non-summer months, the visibility from top of the tower fluctuates and is often so low that entry is not permitted. By scheduling Willis Tower on Day 1, you have a chance to alter plans and revisit in case of zero visibility. Also on a typical summer day thousands of tourists throng the building. The Skydeck and its Ledge is packed to capacity and viewing/photo ops are rushed and limited. By arriving early you can beat the rush and savor your time at Skydeck. The Skydeck opens at 9:00 am in summer and 10:00 am in winter. Plan to spend at least an hour, more if the lines are long.

Standing on the Ledge and seeing the city go about its day thousands of feet below is a thrilling experience

For lunch: Eat the famous deep dish pizza at Giordano’s
Head over to Giordano’s, located a block away from the Willis Tower, for some of Chicago’s famous deep dish pizza. Simple decor and walls covered with Chicago memorabilia invite you to sample the delicious stuffed pizza; friendly staff can help you with the selections.
Giordano’s is located at 223 W Jackson Blvd

Travel Tip: Deep dish pizza takes 30-40 mins to cook, so order an appetizer if you are hungry. The deep dish pizza is stuffed with enormous quantities of cheese and is incredibly filling.

Healthy Alternative: Market Creations, located inside Willis Tower, has one of the most extensive salad bars in the area. They also serve sushi and stir fry.

Majestic lion sculptures grace the Art Institute of Chicago entrance

In the afternoon: Spend an afternoon among the old masters at the Art Institute of Chicago
The Art Institute of Chicago has a vast collection of paintings and sculpture by artists around the globe and is an excellent place to view iconic works or art. The museum features major Impressionist and Post-Impressionist works, African ceramics, American Modernist collection, Renaissance and Medieval art collections, notable contemporary works, Asian collection among others. The 68 Thorne Miniature rooms are highlight of the visit.
The Art Institute of Chicago is located at 111 S Michigan Ave

The museum building has great grounds with large shady trees and fountains.

Travel Tip: Walk over from Giordano’s to the Art institute of Chicago; the 15 min walk passes through the beautiful buildings of Chicago downtown and will help burn off the pizza. Take a photo with the famous lion statues at the museum entrance. Wear walking shoes and plan to spend 2-3 hrs at the Art Institute. Relax by the fountain in the grounds when you are done.

Architectural detour: Walk along W Adams St towards the Art Institute and you will pass by the Rookery building, one of Chicago’s historical landmarks. Drop in to see the stunning lobby and skylight redesigned by Frank Lloyd Wright, the famous architect, in 1905.
Rookery building is located at 209 S LaSalle St

Buckingham fountain runs only in summer and features a beautiful 20 min water display every hour. The center jet shoots 150 feet high in the sky.

In the evening: Relax by the Buckingham fountain and snap your picture in the Bean
Walk to the Buckingham Fountain, located half a mile away, in Grant Park. The fountain runs only in summer and features a beautiful 20 min water display every hour. After dusk the Buckingham Fountain show is accompanied by lights and music. Walk over to the Cloud Gate Sculpture in Millennium Park, 15 min away. Commonly known as the Bean, the stainless steel Cloud Gate reflects Chicago’s famous skyline and the blue summer sky. Visitors enjoy touching the mirrored surface and observing their reflection in the Bean. The Millennium Park with its many attractions including the Lurie Garden, Crown Fountain, Boeing galleries with their contemporary art works, and the steel paneled BP Bridge is one of the most popular things to do in Chicago.  The open air pavilion in the park features free concerts in summer.
The Buckingham Fountain is located at 301 S. Columbus Dr

Cloud Gate Sculpture or the Bean at the Millenium Park in Chicago

Travel Tip: The Bean looks beautiful at any time of the day but is especially stunning at sunset. The Bean also looks spectacular at night when the lit up skyline is reflected on the Bean. The Bean is mostly crowded, best times to avoid crowds are early in the morning or late at night.

Crown Fountain in Millenium Park against the backdrop of Chicago skyline
The bandshell of Jay Pritzker Pavilion in Millenium Park is designed by Frank Gehry

For Dinner: Finish of the day at the nearby outlet Chicago’s famous chain Al’s #1 Italian beef by ordering the famous sandwich. Or go to nearby Berghoff’s, Chicago’s iconic local restaurant, which bears the distinction of being the oldest restaurant in the city.
Al’s #1 Italian Beef is located at 28 E Jackson Blvd while The Berghoff is located at 17 W Adams St

And there, you have just spent a perfect day in Chicago! What is your idea of a perfect day in Chicago? Leave a comment below and let me know. 

Frank Lloyd Wright, the great architect, said of Chicago “Eventually, I think Chicago will be the most beautiful great city left in the world.”
20 COMMENTS
  • Madeline Schuerz
    Reply

    Love this post Ketki. I absolutely fell in love with Chicago when I visited in 2013. Additionally to all the great recommendations in your post I also loved hanging out at Navy Pier. Also Pizza at Giordanos is absolute perfection. My couchsurfing host took me there and I almost died and went to Pizza heaven <3 <3

    1. Ketki R S
      Reply

      Thanks Madeline. I know, isn’t Chicago absolutely gorgeous?! Navy Pier is fun with the funny mirrors and ferris wheel, though touristy. I’d definitely recommend it if you are in the city for more than a day. You are bang on about pizza heaven!

  • Sophie • The Wanderful Me
    Reply

    Cool post! Chicago has always been on my bucket list, although I haven’t had the chance to actually explore the city. I’ve driven through it multiple times and live in Minnesota so I’m not too far away but luck has never been in my favor to visit! I’ll get there soon. Thanks for sharing how to spend the perfect day there!

    1. Ketki R S
      Reply

      You should definitely visit Chicago, Sophie. Doesn’t the skyline look pretty when you drive down the I-90? Minnesota, that’s cool. I have been to the Twin Cities and enjoyed the trip.

  • Emma Le Teace
    Reply

    I’ve been to Chicago many times.. well the airport that is! I’ve never really had the chance to look around properly. Your blog makes me want to make sure I do next time…

    1. Ketki R S
      Reply

      Emma, hope you were at Midway rather than O’hare! O’hare is such a nightmare and always super busy. Do plan a trip to the city this summer, it’s really beautiful.

  • Lia
    Reply

    Gorgeous photos! I’ve been to Chicago a couple of times for work but never really explored the city for fun! This totally made me want some Giordanos though, omggggg yummmmm!

    1. Ketki R S
      Reply

      Thanks Lia. I’m also craving Giordanos and it’s breakfast time 😀

  • Paroma
    Reply

    I am in Chicago right now, across from Millienium park! Thanks for the tips, will check out the Willis tower for sure

    1. Ketki R S
      Reply

      You are welcome, Paroma. Hope you had a great time in the city. Give the Bean my love!

  • Kristin @ Camels & Chocolate
    Reply

    All the times I’ve been to Chicago, I’ve still never been to a) the Bean or b) Willis Tower. Would you say both are must-dos, tourists or not??

    1. Ketki R S
      Reply

      Hi Kristin! Yepp, you just have to visit the Bean. You can skip Willis Tower if you don;t have a head for heights. But IMHO the view is stunning and a complete must-do!

  • Erika
    Reply

    Your love for your city shines through! Love the quotes, especially Oprah’s. 🙂

    1. Ketki R S
      Reply

      Thanks Erika! Chicago inspired everyone, even Oprah! 😉

  • Greta @ Pickles Travel blog
    Reply

    I absolutely love exploring Chicago! It’s such a beautiful city and there is always way more to do than for which I have time! Such a great list of places you’ve compiled.

    1. Ketki R S
      Reply

      I hear you Greta! Even a long weekend is not enough to completely see Chicago.

  • Eleonore
    Reply

    I was in Chicago so long ago and would love to go back and visit again! Thanks for sharing 🙂 Xx, Eleonore

    1. Ketki R S
      Reply

      You should definitely plan a trip soon Eleonore. They keep changing the public arts and so many new great restaurants coming up.

  • Lindsay | The Anthrotorian Travel Blog
    Reply

    I love the deep dish pizza cooking time tip, I never would have thought of that! I’ve never been to Chicago, but this day sounds right up my alley!

    1. Ketki R S
      Reply

      Yeah, many tourists order the deep dish in a hurry and then are disappointed on realizing it takes so long to cook! But it’s definitely worth the wait!

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