August 24, 2025
Chicago, IL
Things To Do
Tavern On Rush
1015 North Rush Street, Chicago, IL 60611
Our first date spot!
Lakefront Trail
Lakefront Trail, Chicago, IL
Urban Kayaks on the Chicago River
Chicago Riverwalk, Chicago, IL 60601
Jake’s favorite summer workout
Chicago River Boat Architecture Tours
465 North McClurg Court, Chicago, IL 60611
Lincoln Park Zoo
Lincoln Park, IL 60614
It’s free and a personal fav for Gill
Torchio Pasta Bar
738 North Wells Street, Chicago, IL 60654
Our favorite neighborhood spot get the short rib pasta.
Bub City
435 North Clark Street, Chicago, IL 60654
Beatrix
519 North Clark Street, Chicago, IL 60654
Portillo's & Barnelli's Chicago
100 West Ontario Street, Chicago, IL 60654
Can’t go wrong here Gill get the tendys, Jake gets the beef, people love the chopped salad. Cheese fries and cake shake are a MUST for first timers.
Asador Bastian
214 West Erie Street, Chicago, IL 60654
Our absolute favorite restaurant in the city it’s a splurge BUT how often are you in Chicago? Not the easiest reservation so book ahead of time. * also where we went to celebrate our engagement
Millennium Park
Chicago Loop, IL 60602
You have to see the bean! The playground is also incredible if you have the kiddos with you!
Navy Pier
600 East Grand Avenue, Chicago, IL 60611
For all the days along the way