For those who want to be outside: Bike paths with (free?) bike rentals, jogging paths, disc golf, soccer fields, sand volleyball courts, and putting greens, all on 95 acres of woods + greens set on the Fox River. For those who want to be inside: basketball courts, 24 hour fitness center, and a 24 hour game room with foosball and ping-pong tables
Start at the Art Institute of Chicago. For the authentic Katherine-Brian experience, pretend to throw your partner into each and every statue as she progressively gets more and more irritated. Then walk around downtown Chicago, Millenium Park, and the waterfront along the Chicago River – keep a brisk walking pace because seeing everything is more important than enjoying the moment with your future wife! Take a break to gawk at the beautiful architecture inside the Chicago Cultural Center, then march your partner 1 mile south, as she complains about how tired she is and how she just wants to sit down already, to see Buckingham Fountain. (It was off when we went in April….) Or visit the Field Museum of Natural History, Shedd Aquarium, and the Adler Planetarium. Close with a romantic date for cocktails at the Signature Lounge on the 95th floor of the John Hancock. Be sure to ruin the mood by endlessly blathering about which streets you can see from here rather than just enjoying the view!
Start your day grabbing coffee in Wicker Park and enjoying a stroll on the new 606 bike path. If it’s warm, check out Chicago’s beautiful lakefront at North Avenue Beach. If it’s April and still cold, bring Katherine there anyways – she really will enjoy the view of the lake even with the freezing cold breeze off it! Then head north to the (free) Lincoln Park Zoo and Botanical Gardens – try to get there an hour before it closes to keep the disappointment in Katherine’s eyes strong. Finally, grab dinner at any of the great restaurants scattered on Chicago’s north side: If you like American food, check out Goose Island brewpub or the Art of Pizza. If you like ethnic food, check out Korea town or India town farther north. And if you’re Brian, take your future wife to a hole-in-the-wall Mexican place on Damen and Milwaukee. (Yes, it’s good food, but maybe not the best date location Brian.)
First, spend 3 hours walking around the fairly average neighborhood of Bridgeport, showing Katherine each and every place you’ve ever walked past as she gets more and more impatient. (Really Brian, you took me down here to show me a hot dog stand?) As you begin to read the regret in Katherine’s eyes, whisk her further south to the University of Chicago for the beautiful neo-Gothic architecture (it actually is quite nice). If you can walk even faster than me and are even more ready to overwhelm your partner, head east to Jackson Park and the Point to enjoy good views of the Lake and downtown Chicago, or check out the Museum of Science and Industry. Then head back north to Chinatown – be sure to drive, sit in traffic on I-90, and spent 30 minutes looking for parking rather than, say, renting bikes and taking the enjoyable lakefront trail north. Enjoy an excellent dinner in Chinatown, with a post-dinner stroll into the Chinatown shops on Archer or Wentworth streets to close the day.