Recently, I was in Chicago for the American Historical Association’s Annual Meeting. As it does every time, Chicago tantalized me with its tasty food spots, wonderful cultural venues, and splendid shopping.

During the Industrial Revolution, Chicago’s access to shipping and railroad routes gave it a prime location to be part of the nation’s growing industrial output. The city rebuilt in a modern fashion after the Great Fire of 1871, laying the blueprint for some of the buildings one can see today. Chicago earned the moniker “Second City” and great acclaim when it hosted the 1893 World’s Fair. The city showed off its riches, culture, and the architectural genius of Burnham & Root during that exposition—the remnants of which are still around. I love wandering the streets of Chicago and exploring its past and present. If you go there, here are some of my favorite places to eat and fun things to do in Chicago:

Places to Eat in Chicago

  • XOCO—a trained anthropologist, chef Rick Bayless has spent a good deal of his life immersed in Mexican culture. Savor the succulent short rib and pickled jalapenos in the Pepito torta. And don’t miss dessert—the chocolate sauce for the churros is almost a religious experience.
  • Eataly—this “Italian” market with numerous restaurants within its walls consistently has fresh pasta, authentic pizzas, and a nice selection of vegetarian dishes, fish, meat, and more. I like the bucatini all’Amatriciana—it’s the best I’ve had in the States.
  • Italian Village—Opened in 1927, this restaurant serves up large portions of just about any type of traditional Italian-American fare that you can dream of. When hubby and I were there last, we were given a romantic little alcove to sit in where we could have an intimate dining experience.
  • One look at a Chicago Deep-Dish Pizza and you will know why they’re called pies. These concoctions are at least an inch thick and filled with cheese, toppings, and sauce. Each Chicagoan has their favorite; I’m going to avoid that debate, but I recommend Lou Malnati’s, Giordano’s, Gino’s East, or Pequod’s (if you’re outside the Loop).
  • Al’s Beef—Tender sliced beef with spicy or sweet giardiniera on a hoagie roll, Italian beef is tasty and filling. At Al’s you can choose to have your sandwich dipped or double-dipped in rich au jus; if you do, be prepared to hunch over to avoid wearing Italian beef down your front.
  • Portillo’s is a good place to get the iconic Chicago dog, but don’t even think of asking for ketchup on this poppy-seed bun. You won’t miss the tomato condiment though amidst the mustard, relish, tomatoes, pickle, onions, and peppers this dog boasts.
  • Exchequer—located in a building that has housed restaurants since the “Roaring 20s” (it’s rumored Al Capone patronized one of them), the Exchequer has been in business since 1969. I dined on really, really, good chicken and Grecian potatoes while reading historic news articles on the walls.
  • Pittsfield Cafe—this small restaurant/deli serves tasty food from breakfast to dinner. I enjoyed a tender, lean, hand-sliced corned beef sandwich. The meat tasted as if it had been roasted for hours. If corned beef isn’t up your alley, the cafe has a full menu to satisfy many tastes.

Things to Do in Chicago

  • The Chicago Cultural Center a.k.a. the “People’s Palace” is not to be missed—gorgeous architecture, a Tiffany dome, and cultural events abound.
  • The Field Museum of Natural History is filled with Egyptian artifacts, dinosaur skeletons, gems, meteorites, cultural items, and taxidermied animals from all over the world. The museum is known for its Tyrannosaurus Rex skeleton called “Sue.” A new permanent exhibit was just opened for her. Check out Sue’s new home. Other institutions on the same campus as the Field Museum are Shedd Aquarium and Adler Planetarium.
  • Architectural Tour—Chicago is a city to see by foot (and by water if weather permits) and I recommend booking a walking tour. I’ve used the Chicago Architecture Foundation in the past and have been quite pleased. Whether you go with a tour or self-guided, make sure you see: Chicago Water Tower (there is a free photo gallery inside), Fourth Presbyterian Church, Tribune Tower, the Wrigley Building, Buckingham Fountain, the Palmer House Hotel (This is my favorite place to stay. Built in 1873, it has a grand lobby with a breathtaking frescoed ceiling and a Tiffany-designed Peacock door off one entrance.), arch of the former Stock Exchange (behind Art Institute), Carbon and Carbide Building, Willis Tower, and the Rookery.
  • Take a walk in Millennium Park and enjoy the outdoor art installations. Don’t miss an opportunity to take your picture in the “Bean” (Cloud Gate by Anish Kapoor) or splash around in Crown Fountain by Jaume Plensa.
  • The stately residence of the Driehaus mansion allows you to see how the rich lived in Gilded Age America.
  • The Art Institute of Chicago is another feast of the senses. The institute has an impressive collection of Impressionist art, as well as notable ancient artifacts, the famed American Gothic by Grant Wood, and over 3500 European works dating from the 12th through the mid-20th
  • Journey down to Navy Pier and ride the Ferris Wheel (first debuted at the 1893 Chicago World’s Fair).
  • Take in a show, like Hamilton or the Second City comedy troupe, or see a Cubs baseball game at Wrigley Field.
  • At the Federal Reserve Bank of Chicago, visitors can go inside to the free “Money Museum” and learn about the Federal Reserve System, see historical currency, and engage with quite interesting interactive exhibits.

Chicago is a culturally-rich city where history is honored throughout the town and food offerings are renowned. The Windy City has great architecture, entertainment, museums (there are so many other cool ones than those I mentioned), and shopping. Michigan Avenue a.k.a. the Magnificent Mile has three vertical malls (Shops at North Bridge, Water Tower Place, 900 North Michigan) and retailers of all price points up and down the street. If you’re looking for mid-lower range shops, try State Street with a huge Macy’s in a historic building, Block 37 vertical mall, and numerous stand-alone stores. Chicago provides seemingly endless retail therapy!

I hope you enjoy all the fun things to do in Chicago. Happy travels!

Related blogs:

My Top Five Things to Do in Chicago: https://roaminghistorian.com/2018/04/22/fun-things-to-do-in-chicago/

Three Perfect Days in Chicago Part One: https://roaminghistorian.com/2015/05/29/places-to-visit-in-chicago/

Part Two: https://roaminghistorian.com/2015/05/29/visit-chicago/

Part Three: https://roaminghistorian.com/2015/05/30/chicago-tourism/

Like what you just read? You can support me by following my blog and leaving comments–I love to hear from my readers. Happy travels! Amy

If you enjoy our pictures, please check out our photography shop on Etsy where you can purchase our prints. We don’t have all of our prints listed on our Etsy site, so don’t hesitate to contact us if you see a picture in a blog post that you would like to order.