Have you ever been to Chicago? Do you like deep dish pizza? Do you not like deep dish pizza? Doesn't matter. This one is the best. Bootes is still salty that it took 4 years before Crystal took him here. (Bootes is being dramatic, it was 3 years.)

Looking for a classic Chicago dog? How about an Italian beef sandwich? Portillo's is Illinois's most popular restaurant chain and serves these Chicago classics. Don't sleep on the onion rings and chocolate cake - these are Crystal's favorites. This location is just one of many in Illinois!

Coffee good. Me need coffee. Drink coffee. Also they have barbecue for some reason.

Do you like good beer? It's one of our favorite taprooms in the city, and we live just blocks from it! You can stop by for a beer or take a tour. They have tours Fri-Sun at 1PM, 3PM, and 5PM (online reservations required.) Let them know Crystal sent you!

If you love art, this is a must! The renowned Art Institute of Chicago is one of the country's oldest and largest art museums. We had a fantastic opportunity to take engagement photos at this beautiful museum. Millenium Park is also nearby, so if you want to see a shiny big bean, that's where it is!

Do you like weird art? Do you just go where your girlfriend tells you to go? Do you know that she'll always lead you to the right place? Try one of our first date spots in Chicago.

Known for its improv and sketch comedy, the venue has hosted some of the biggest names in comedy, including Tina Fey, Steve Carell, Bill Murray, and many others. An icon of the comedy scene, you'll have a good laugh at Second City.

It's probably unsurprising to hear that Crystal and Bootes enjoy going to science museums, and Chicago has an amazing one!

The Field Museum is a natural history museum and one of the largest museums in the world. You can meet Sue the T Rex, the namesake of an outstanding IPA beer series by Toppling Goliath Brewing. The Field Museum is part of Chicago's Museum Campus, which also includes the Shedd Aquarium and the Adler Planetarium.

If shopping is on your agenda for the weekend, the Magnificent Mile ("Mag Mile") is the place to do it. Mag Mile offers a mix of high-end boutiques, international brands, and flagship stores.