If the ’rents love big buildings…show them you’re a lifelong learner on the Chicago Architecture Foundation’s Architecture River Cruise (Departs from 112 E Wacker Dr, 312-922-3432, architecture.org, $32, reservations a must). The CAF offers 5:30pm cruises on Thursdays, Saturdays and Sundays through September 29. Expert docents make this a fascinating tour, and you and your sweetie can steal a few smooches while the ’rents are ogling the skyscrapers. If 90 minutes of architectural history doesn’t sate them, proceed to dinner at the Gage (24 S Michigan Ave, 312-372-4243, thegagechicago.com). This excellent restaurant occupies the first floor of a gorgeous building Holabird & Roche completed in 1890, next door to one with a facade by Louis Sullivan.
If your architecture-loving potential father-in-law gets seasick or Dave Matthews is in town…start the evening with cocktails and spectacular skyline views at the Hancock Center’s Signature Lounge (875 N Michigan Ave, 96th floor, 312-787-9596, signatureroom.com/signature-lounge) in Streeterville instead. Are heights a problem, too? The Chicago Riverwalk (South bank of the Chicago River between Franklin St and Lake Shore Dr, cityofchicago.org/riverwalk, free), which stays open until 11pm through mid-October, offers its own impressive vistas. If the conversation flags, grab a drink at Cyrano’s Café and Wine Bar on the Riverwalk (233 E Lower Wacker Dr, 312-616-1400, closes around October 8, depending on the weather) or Bin 36 (339 N Dearborn St, 312-755-9463, bin36.com). Just don’t loosen up so much you start talking about politics or religion. If tonight goes well, you can try those topics at Thanksgiving dinner.
If the parents are happy you’re a fellow culture vulture (or they start interrogating you about your career prospects)…kill the next few hours at the Goodman Theatre (170 N Dearborn St, 312-443-3800, goodmantheatre.org, $25–$76), where the musical Animal Crackers runs through October 25. Trust us: The Marx Brothers are more likely to bridge the generation gap than whomever’s playing the Empty Bottle. Vivere (71 W Monroe St, 312-332-7005, italianvillage-chicago.com) doesn’t serve duck soup, but the Italian restaurant’s stellar wine list should lift everyone’s spirits before the show.
If your S.O.’s mom admits to a crush on Joshua Bell…head over to the Chicago Symphony Orchestra (Symphony Center, 220 S Michigan Ave, 312-294-3000, cso.org, $22–$199) for the virtuoso violinist’s concerts October 7–10. Other CSO fall season highlights include a visit from pianist Garrick Ohlsson and performances of Brahms, Mendelssohn, Mozart and Schumann. If your S.O.’s dad is like our dad, just grab tickets for one of the John Williams Movie Music Spectacular concerts November 27–29. Spring for dinner at romantic Rhapsody (65 E Adams St, 312-786-9911, rhapsodychicago.com) next door, and everyone will be too distracted by the top-notch desserts to notice you and your honey playing footsie under the table.
If the ’rents are footing the bill…dress to impress at the Lyric Opera (Civic Opera House, 20 N Wacker Dr, 312-332-2244, lyricopera.org, $32–$187), where Charles Gounod’s Faust puts your post-grad escapades in perspective from October 5–November 7. Splurge on dinner just across the river at Paul Kahan’s James Beard Award–winning Blackbird (619 W Randolph St, 312-715-0708, blackbirdrestaurant.com) or try the Civic Opera House’s elegant new in-house restaurants, Florian Opera Bistro and the Sarah and Peer Pedersen Room, which open (to ticketholders only) September 26.
If the economy’s hammered their 401ks—or they don’t have the patience for supertitles…treat them to dinner at Shawn McClain’s South Loop steak haven Custom House (500 S Dearborn St, 312-523-0200, customhouse.cc). We also love Hackney’s (733 S Dearborn St, 312-461-1116, hackneysprintersrow.com) for its relaxed atmosphere, extensive list of beers from local breweries such as Metropolitan and Half Acre, and hearty American food at reasonable prices. Just a few blocks east, 20-year-old Buddy Guy’s Legends (754 S Wabash Ave, 312-427-0333, buddyguys.com, $10 cover Sun–Thu; $15 Fri, Sat) serves up cool jazz until long past everyone’s bedtime.
The first date | The meet-the-parents date | The get-me-out-of-the-doghouse date | The cheap weekday date | The under-the-radar, underground date | The solo date | The true bromance/girlfriends date | The special-occasion date