The best Chicago one day itinerary is a mix of main attractions, good food, and a little spontaneity.
Chicago is the biggest city in the midwest and is teeming with cultural attractions like Cloud Gate (The Bean) and the Art Institute of Chicago. Not to mention, the city hosts many excellent coffee shops, great shopping, and that quintessential deep dish pizza.
Chicago is also home to the iconic Skydeck Ledge that sits on the 103rd floor of the Willis Tower (the tallest building in the Midwest). The city borders Lake Michigan and is a good mix of cityscapes with a few natural parks too.
A few years ago I had the chance to visit the city with my mom. We only had one day of sightseeing during our visit and we definitely made the most of it. An easy one day itinerary in Chicago is the way to go if you have limited time to spend in the Windy City.
Without further ado, here are my picks for the ultimate one day Chicago Itinerary.
- Coffee and Breakfast
- Riverwalk
- Shopping (optional)
- Giordanos Pizza
- Skydeck Willis Tower
- The Bean
- Museum of Art
- Afternoon Coffee
Breakfast in Chicago – Sit Down vs. Coffee and Pastry
When it comes to breakfast, coffee is the main character in my book. So in choosing our first stop, I went with a place based on the coffee and shop vibes, and as a secondary option, something for breakfast.
Coffee Shops to Visit During Your One Day Chicago Itinerary
In true form, we didn’t opt for one of the many well-known sit-down breakfast spots Chicago has to offer, but instead grabbed a pastry and coffee at Intelligentsia Cafe. This cafe was located along our walk to the Skydeck from our train stop in the city.
- Intelligentsia Coffee Monadnock Coffeebar, Monadnock Building, 53 W Jackson Blvd, Chicago, IL 60604
The pit stop was just what we needed after an early morning flight from New Orleans, LA. There are plenty of coffee shops in the area along the walk towards the Skydeck if you’re taking the public transport route.
Hero Coffee is a tiny shop tucked away in an alley with outdoor seating and a bright COFFEE sign that you can’t miss, and Dollop Coffee Co. is another option, which serves coffee and loaded bagels.
Sit-down Breakfast Spots
If you’re more into a big sit-down breakfast, Chicago has plenty to offer. Checkout:
- Sunny Side Up Breakfast & Lunch, 42 E Superior St, Chicago, IL 60611
- Yolk – Streeterville, corner of Grand & McClurg, 355 E Ohio St, Chicago, IL 60611
- Batter & Berries, 2748 N Lincoln Ave, Chicago, IL 60614
Each spot has over 2,000 reviews on Google and a 4.5 rating or higher.
If your plan follows this itinerary, these breakfast spots are all close to the Skydeck:
- Sunny Side Up Breakfast and Lunch: 1.8 miles / 10 minutes drive from Skydeck
- Yolk – Streeterville: 2.2 miles / 10 minutes drive from Skydeck
- Batter & Berries: 6 miles / 20 minutes drive from Skydeck
Riverwalk
After coffee and breakfast, spend some time walking around downtown and taking photos, or head straight to the riverwalk. There are a few spots with some street art along the way and the Riverwalk gives you a great view of the city.
This is an easy itinerary item to work into the list and allows for some time to truly just sightsee. You can work in some shopping too if that’s something you’re interested in.
Shopping Magnificent Mile + Starbucks Reserve
We didn’t have time to shop on our trip because our timeline only allowed room to see the Museum instead of shopping. If you’re more inclined to retail therapy, you can certainly opt for some shopping.
The Magnificent Mile is the most notable shopping area in Chicago. It offers a large selection of department stores and designer stores alike, all located along one strip. The Magnificent Mile is also host to one of the biggest (if not the biggest) Starbucks Reserves in the U.S.
Basically, a Starbucks Reserve is a boutique Starbucks experience. I normally skip Starbucks and opt for a more local shop, but the one time I stumbled on the Starbucks Reserve in Seattle, I was very intrigued and really enjoyed the experience. Most Starbucks Reserves include a huge facility and in-house roastery that is served fresh on the spot. You can expect the drinks to be even more expensive at a Reserve, but to have that in-house roasted flavor that many small shops/roasteries have.
The Magnificent Mile is only 1.6 miles from Intelligentsia Coffee and 1.9 miles from the Skydeck.
Giordano’s Pizza – Perfect Lunch Spot before the Skydeck
After shopping or sightseeing, it’s high time to get some lunch. There are many places to eat around town, but if you’re into a slice of deep dish pizza, Giordano’s is a good option and it’s only a 2-minute walk to the Skydeck.
Giordano’s is located at 223 W Jackson Blvd, Chicago, IL 60606, and holds over 8.5k Google reviews. Be aware that you’ll have to budget a couple of hours if you want to order a deep dish and wait for it to be cooked.
Since we only had one day, we opted for the mini deep dish pizzas they have pre-made that came with a side salad. I’m going to be honest, the pizza we had wasn’t the best. It was a mini deep dish, sure, but it wasn’t fresh and therefore nothing to write home about. If I had more time, I would have waited so I could order the real thing, or tried to order ahead of time.
Another pizza option is Pequod’s Pizza located at 2207 N Clybourn Ave, Chicago, IL 60614. Pequod’s has over 11K reviews and from the look of the restaurant, looks like a hole in the wall place.
Skydeck Willis Tower – A Must-See for a On-Day Chicago Itinerary
The Skydeck Ledge is a glass box suspended over 1,000 feet in the air, hanging off the 103rd floor of the tallest building in the city. Currently, the experience costs between $30 – $38 for a time slot. It is unfortunately worth the hype. The views of the city are unparalleled and the photo opportunity is one-of-a-kind.
Be prepared to deal with some crowds. Although the time-slot ticketing system does help reduce how much foot traffic is in the tower at once. Keep in mind that you only have about 60 seconds to spend out enjoying the Skydeck Ledge. You can easily wait in line for more opportunities to step out on one of the 4 Skydeck Ledge spots, however.
Cloud Gate AKA The Bean
Next on the list is Cloud Gate, an art exhibit commonly referred to as ‘The Bean’. This item is set in the middle of a courtyard that is a part of Millenium park. Expect crowds to be swarming around the Bean at most hours. This outdoor exhibit is probably the most photographed item in the whole city.
Seeing the exhibit and taking some photos honestly doesn’t take very long. You just have to wait for a good opportunity. Some fun ideas for shots include: taking a reflective photo of you and your friend or family, asking someone to take a picture of you in front of the bean reflecting the city in the background, and just a regular photo standing in front of the Bean.
The Art Institute of Chicago – An Excellent Site to See during a One Day Chicago Itinerary
Last on our list of attractions is the Art Institute of Chicago. This museum offers a wide range of art exhibits and extremely popular art pieces including:
- A Sunday Afternoon on the Island of La Grande Jatte – Georges Seurat’s most famous work.
- American Gothic – a 1930 painting by Grant Wood
- Nighthawks – a 1942 oil on canvas painting by Edward Hopper
- Paris Street; Rainy Day – 1877 oil painting by the French artist Gustave Caillebotte
- Two Sisters (On the Terrace) – Two Sisters or On the Terrace is an 1881 oil-on-canvas painting by French artist Pierre-Auguste Renoir
- Self-Portrait and The Bedroom – Vincent Van Gogh
- Water Lilies – Claude Monet
- Water Lily Pond – a painting from 1900 by Claude Monet
The institute can easily take up an entire day of seeing all the wings of the museum, but you can also opt to spend a few hours in only the exhibits you really want to see. The price for an adult ticket is $25 for non Illinois-residents.
You can also opt for buying a ticket at a discount for the last few hours of the day, which is $18 or so. This is the route we went since when we arrived we were minutes away from the discounted price. Also, we knew we mainly wanted to see the impressionism exhibit. We had plenty enough time to see all the paintings listed above.
Afternoon Coffee
At this point in the ultimate Chicago one day itinerary, you’re probably feeling a little tired of running around the city having a full day. Afternoon coffee at 5 pm, which is the time the museum closes, is an easy next choice.
Grab a cup across from Cloud Gate (the Bean) at
- Fair Grounds coffee: 12 S Michigan Ave, Chicago, IL 60603
- Momentum Coffee Millennium Park: 11 N Michigan Ave, Chicago, IL 60602
- Goddess and the Baker, Wabash: 33 S Wabash Ave, Chicago, IL 60603
- Intelligentsia Coffee Millennium Park Coffeebar: 53 E Randolph St, Chicago, IL 60601
- Peet’s Coffee: 10 S La Salle St, Chicago, IL 60603
Intelligentsia is around the corner from Millenium Park, but Fair Grounds and Momentum Coffee are right across the street. Millennium Park and the Bean have also located a short, 4-min walk to the Art Institute.
Dinner in Chicago
During our Chicago one day itinerary, we actually ended up taking our bus and train back to our hotel’s area for dinner. We had time to rest up, change and grab drinks and dinner at the hotel restaurant. It was a pretty utilitarian end to the day.
If you’d prefer to grab something while you’re out, here’s a list from nearby Millenium park. Many of the restaurants close by are on the expensive side of things, but there are some more affordable options as well.
- Cindy’s Rooftop: 12 S Michigan Ave, Chicago, IL 60603 ($$$)
- The Dearborn: 145 N Dearborn St, Chicago, IL 60602 ($$)
- Roka Akor: 456 N Clark St, Chicago, IL 60654 ($$$)
- Sultan’s Market: 2057 W North Ave, Chicago, IL 60647 ($)
- Jim’s Original Hotdog: 1250 S Union Ave, Chicago, IL 60607 ($)
And don’t forget, you can opt for another round of deep dish pizza at Pequod’s Pizza located at 2207 N Clybourn Ave, Chicago, IL 60614. It is only a 13-minute walk/ 4 min drive from the Bean.
Chicago – One Day Itinerary Bottom Line
At the end of the day, downtown Chicago is an easy place to spend a whole weekend in. If you have more time and can take things at a slower pace, go for it! But, if you have limited time to sightsee, I think this one day itinerary is one of the best that touches on most of the top spots in the area.
