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Things to do in Chicago | A Perfect Day in the Windy City

Chicago is a city known for its deep-dish pizza, friendly neighborhood bars, and top-notch museums. With so much to do in Chicago, it is important to have a list of things to see so you don’t miss out. We lived in this city for years and below are some of our best tips for one perfect day in Chicago!

If you are in a hurry, we also have a cheat sheet below of three things you can’t miss if you visit Chicago!

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Things to do in Chicago

Chicago cheat-sheet: 3 things you can’t miss if you go

Museums and Millennium Park are things every tourist wants to see. But these are the top three things you absolutely have to do before you leave Chicago.

  1. Go to Chicago oven and pizza grinder co. The food is worth the wait. Get a giant bottle of Chianti and your own pizza. Wear stretchy pants – you will need them
  2. Take a water taxi to Chinatown. If it is nice out hop down to the water taxi. It runs from the loop to Chinatown and back. Buy a two-way ticket. It’s cheaper than a taxi and the architecture tour, but you get all the views.
  3. Go to Snicker’s Bar or Old Town Tavern. Two Chicago staples. Snicker’s bar is a dive bar in River North. Despite being in one of the most expensive areas of Chicago, Snicker’s sells beers for $3. Old Town Tavern is cash only, and extremely unique. This dive bar boasts hilarious art and a cozy vibe. 

How to spend the perfect day in Chicago

Chicago Cityscape

A day in Chicago itinerary

Chicago is a bustling city with a lot to see. You can’t see everything in one day, but you can experience some of Chicago’s most iconic sites if you follow this itinerary.

Best breakfast options in Chicago


The city offers some amazing breakfast spots and here is a full list of the best breakfast spots in Chicago.  

Chicago mornings are bustling. If you prefer something light and on the go, start off your morning with a coffee and pastry at Firecakes. They are located in the heart of the city and have unique donuts with freshly brewed coffee and espresso drinks.

If you want to live like a local, here is a hidden gem: in the bottom of the John Hancock tower, next to the Cheesecake factory, there is a small Italian grab-and-go breakfast spot called Espression by Lavazza. They have excellent coffees and pastries on the run.

For a sit-down experience, we recommend Yolk or Eggy’s. Yolk has a location in nearly every neighborhood of interest and their breakfast has something for everyone. The line can get long though.

If you’re looking for a more hidden breakfast spot, check out Eggy’s in Lakeshore East. Hidden in a neighborhood park, Eggy’s always has an open table and their food is eggsceptional.

Visit a Museum

Chicago is home to all sorts of museums and many rank among the best in the world. Among the most notable are the Art Institute, the Field Museum, and the Shedd Aquarium.

The Shedd Aquarium opens the earliest and is home to 32,000 ocean lifeforms and animals. Big draws include Pacific white-sided dolphins, beluga whales, sharks, stingrays, and otters. The tours at the aquarium let you get up close and personal with most of them. The Shedd Aquarium is located in Museum Campus Park and open Thursday through Monday from 9am to 5pm and closed Tuesday and Wednesday. 

About one mile or a 20-minute walk from the aquarium you’ll find the Art Institute Chicago; another stellar museum choice. It is one of the best Art Institutes in America and the #1 rated attraction on TripAdvisor when visiting the city. The museum houses art from famous artists such as Picasso, George Seurat, and Van Gogh. The Art Institute is next to Millenium Park and is open from 10:30-5pm Saturday-Wednesday and 10:30-8pm on Thursdays and Fridays.

Other museums to visit are the Shedd and the Field Museum in museum park. You can get all your museums done under one pass that will save you time and money, which is the Chicago CityPASS.

Explore Millennium Park

Spend a Perfect Day in Chicago

After you spend a few hours exploring a museum or two, it’s time to visit more of Millennium Park. This park is in the heart of Chicago making it the perfect mid-morning spot. View the bean and water fountains and listen to free live music.

Millennium Park is a giant park in the heart of Chicago. Millennium Park has statutes, a garden, and the infamous bean.  Stop by the bean and see your reflection.  You will probably need around 45-minutes to see the park. After glancing at the statutes and art exhibits, there is not much else to do. Take in the views of the city and take some pictures. 

Lunch in Chicago

Flaco’s Tacos is a great spot with crispy tacos and handmade tortillas. They have the best guacamole and quesadillas in town. It’s the perfect lunch spot because they make great food without all the fuss of a long sit down lunch. They have three locations and the Printers Row restaurant at 725 S Dearborn Street would be the most convenient for this perfect day itinerary. 

From Millennium park walk north on Michigan Avenue. Take in the shops, the Wrigley Building, and the Hancock Tower. Stop in for a quick drink on top of the Hancock and take in all the views. You only need about a half-hour up here, so have your drink and get moving! There’s a lot more to see.

Afternoon Shopping

If you’re looking for shopping, you are in the right place. A hidden secret – State Street is much better shopping than Michigan Avenue. It’s where all the local’s shop. You avoid the tourists, the prices are lower, and the stores are more affordable.

If you’re not into shopping, the best way to spend your time is exploring the neighborhoods. The best way to get around town is the “L” A train that connects all the best neighborhoods in the city.

Some neighborhoods to spend time in are:

  • River North: the hip mid-20s neighborhood with overpriced condos and clubs. Also some pretty great restaurants.
  • West Loop/Fulton Market: The newest boom in Chicago, these neighborhoods are for the foodies and once hipsters.
  • Lincoln Park: the post-college neighborhood is filled with bars, fast restaurants, and
  • Gold Coast: otherwise known as the “viagra triangle” the gold coast has some of the most legendary restaurants in Chicago. Enjoy the shops and fancy cars.
  • South Loop: a low-key neighborhood with good eats and casual dining. South Loop is well-located so you can cruise up to the north or down south in ease.
  • Lakeview: one of the more northern-downtown neighborhoods, Lakeview has large parks, including a dog park, and great food.
  • Chinatown: located right off the redline, or the water taxi, Chinatown has excellent restaurants and shops. Well worth the visit!

Nighttime in Chicago

Best Choices for Dinner

For the trendy spots head to Fulton Market or West Loop. For standard Chicago fare, stick near River North and Gold Coast. Just want a good old burger? Head to the Billy Goat Tavern. This place is legendary – order fast or they will order for you.

Best dinner spots in Chicago

There are so many great restaurants in Chicago, and there are new ones popping up every day. Chicago has always been known for steak and seafood, but now it’s becoming premier small plates and boutique restaurant destination for culinary masterminds.

This list is hard to narrow down. Chicago is definitely a dinner city and there is a restaurant for every taste.

Small plates, big appetite. Café Iberico is the best small plates restaurant in Chicago. They have excellent small plates perfect for sharing and excellent house-made sangria.

Best steak. In Chicago we can’t choose just one steak restaurant. The top three are Chicago Cut, Gene & Georgetti, and 437 Rush. Go to all three if you can, we can never pick one.

You must have pizza. One thing you must do before you leave Chicago is try the pizza. Deep dish pizza is a ritual in Chicago, but you have to go to a classic spot. Pizzeria Due is our favorite to recommend to visitors. Pizano’s is also a top contender. And if you’re going for something more standard, Lou Malnati’s has you covered.

After Dinner

After dinner either head back up to the Hancock for fireworks (if it’s a Wednesday or Saturday), or head nearby the Chicago River. On the river, there are numerous good restaurants and rooftop bars. Londonhouse is the hot spot for summer!

Fun facts about Chicago

Chicago has a vibrant history. From Native American warfare to mobsters, there is history around every corner. Here are some lesser-known facts about Chicago.

  • Native American battle. If you look closely on the Michigan Avenue bridge you can see plaques detailing the battle of Fort Dearborn.
  • Mobsters. Probably the most well known fact, but Chicago was home to Al Capone. The city offers Al Capone tours so you can see the sites he visited.
  • Sports. Chicago is home to a NFL, NHL, NBA, and two MLB teams. Chicago is a big sports town.
  • The Great Chicago Fire. In 1871 a large fire roared through the city. All the rubble was pushed into Lake Michigan. All the land past Michigan Avenue is a remnant of the fire. Michigan avenue was actually where Chicago met the lake until this fire.
  • No Ketchup. It is a disgrace in Chicago to put ketchup on your hot dog. Don’t do it, don’t ask for it.

Where to stay in Chicago

Chicago is home to every hotel you can imagine. It’s really a pick your poison and comfort situation. Recently, Chicago has developed a whirlwind of boutique hotel options that provide a unique, charming atmosphere to your stay.

Some of my favorite options include the Hotel Lincoln, The Publishing House Bed and Breakfast, Freehand Chicago, and the Robey. All hotels offer varying options of affordability to luxury. These options are a great way to get away from the typical standard-issue hotel.

Hotel Tip: The best area to stay is in River North or Streeterville. These areas are central and easy to get around. Ideally, stay close to the train to save on cabs.

Best time to visit Chicago

Summer, fall, or over the holidays. There is something magical about Chicago in December. They put on a Chriskindlemarket complete with handmade ornaments. But the best time to explore is in the late summer, early fall. Avoid spring. It’s nasty.

Tours and Day Trips From Chicago

One of the best ways to see Chicago’s top attractions at significant savings is with the Chicago City Pass

hop on hop off chicago
chicago pass
Chicago go pass

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