Things To Do

Wrigley Field

Wrigley is the best ballpark in the country and home of the Cubs...but we really only go here to watch the Mets, Mariners, and take in a few great James Taylor and DMB concerts. If you're here Sunday June 23rd, please join us to see the Mets in honor of Michelle's dad Jack, who was a HUGE fan. Let's Go Mets!

Hamilton at the CIBC Theatre

Hamilton is playing here and ticket prices were going down last we checked. Michelle surprised me with tickets for my birthday and we can't wait to see it again. Highly recommend!

Portillo's Hot Dogs

Hot dogs and Italian beef sandwiches are a Chicago staple. This place does 'em like nobody else. This is usually the first stop requested after an airport pick up for visiting family members in the Thompson-Dolen clan. There are several locations around Chicagoland. Best. Fries. Ever.

Navy Pier

Navy Pier is right on Lake Michigan in downtown Chicago. During Tom's first visit to Chicago we stopped here to take in the great view of the Chicago skyline from the ferris wheel. There is a free trolley service to take you here from Michigan Avenue with schedules and pick up locations listed online. There's a children's museum here, boat cruises, shops, food and rides. Fireworks in the evenings on Wednesdays and Saturdays.

The Art Institute of Chicago

Redhead Piano Bar

Michelle is a big fan of piano bars! This one is open until 4am for a great time.

Kitty O’ Sheas

This is where we spent St. Paddy's Day last year! Great Guinness, Corned Beef Sandwiches, and lively music on the weekends. A fun Irish bar located on the ground floor of the Hilton on Michigan Avenue.

Mia Francesca

A Jack Thompson favorite and he knew good Italian food! They have a few locations in the city and in the suburbs. We went on a few dates here, including dinner with all the Thompson girls the night we got engaged!

Egg Harbor Cafe

We LOVE going out to breakfast! Egg Harbor is a great place for breakfast and lunch with a few locations around the Chicago area. We've had many, many, many great breakfasts here!

The Second City

This made the date list when Tom first visited me in Chicago. So many famous comedians started their careers here and went on to Saturday Night Live, movies, TV shows, etc. If you like sketch comedy and improv this is a Chicago institution!

Buckingham Fountain

A Chicago landmark that is simply beautiful at night.

Buddy Guy's Legends

Have a drink and listen to some great Chicago blues music! The legendary Buddy Guy may make a cameo and perform. This was another fun and memorable date night for us after we saw the Packers beat 'Da Bears!

House of Blues Chicago

Touristy but an iconic Chicago blues bar. They have a Gospel Brunch on Sundays we hope to check out sometime soon.

Chicago Architecture River Cruise

A great way to learn about Chicago's architecture while enjoying a cruise down the Chicago River!