Chicago is one of my favorite places. I interned there in college and quickly fell in love with the city. Since my internship, I’ve returned twice, once as a newly engaged couple and most recently with my husband this fall. Although I’d lived there before, I spent a lot of time researching where we should eat and what we should see before our trip. Below is a map of the places we visited this time around.

View Misc – Chicago in a larger map.

This trip was a great one, but there were a few things we didn’t do that are fantastic. Here’s the complete list of my favorite things to see and do in Chi-town.

• Go to a Cubs game
• Visit the Art Institute
• Shop on Michigan Avenue
• Experience a whole new world at the Shedd Aquarium
• See Chicago at new heights at the John Hancock Observatory
• Take a walk on the beach
• See a show at Second City

Be sure to visit Chicago’s Convention & Visitors Bureau Web site to see what’s happening during your stay. Trust me, the city has some great events, particularly in the summer.

My husband and I ate like pigs in Chicago. It was fantastic, but a little ridiculous. Take advantage of our extensive research and check out at least one of these restaurants:

• XOCO: This is a Rick Bayless restaurant. While we were there, he was working, and I was starstruck. The food and restaurant are pretty casual, but the food is great. Try this as a lower cost alternative to his other restaurants.
• The Purple Pig has been recognized by Bon Appetit and slew of other incredibly smart foodies. It’s a little pricey, but well worth the money. Choosing from their list of small plates can be intimidating, but you can’t go wrong. My husband had the milk braised pork and I had the pork steak. Both were unbelievably delicious.
• MORE is a lovely cupcake shop. The flavors are unusual, yet familiar. They provide great fuel after a day spent shopping on Michigan Avenue.
• Castel Gandolfo serves pizza. It’s not Chicago-style pizza, but don’t let this turn you away. We choose a goat cheese and prosciutto pie that I still think about. As a matter of fact, I’m craving it right now.
• Franks ‘N’ Dawgs is one of the three, most highly respected hot dog joints in Chicago. Wiener Circle and Hot Dougs are also supposed to be amazing, but I’ve never tried them. I can only vouch for Franks ‘N’ Dawgs. Their inventive combinations will redefine how you think about hot dogs.
• Last, but not least, we had a romantic dinner at Table Fifty-Two. The chef, Art Smith, does up-scale Southern food. Everything was wonderful, but the two most amazing parts of the meal were the things we didn’t order, a simple, but complex goat cheese and scallion biscuit and a deviled egg. This was my favorite place we ate, but I should warn you, it was the priciest.