Almost all trips fit in time for discoveries, and some roads have dead ends. Here’s how a quick overnight in Chicago unfolded this month.
12:30 p.m. Thursday – My Van Galder bus arrives at Union Station about 3.5 hours after the ride from Madison began. (I’m quite fond of Chicago but have no interest in driving there or paying beaucoup bucks to park.) coachusa.com, 608-752-5407
Tent awnings in front of Willis Tower, the skyscraper formerly known as Sears, interrupt my walk toward Michigan Avenue, but this midday market has few vendors. There also is no wait to zip up to the 103rd floor SkyDeck, whose all-glass observation ledge extends 4.3 feet over Wacker Drive. Another option: Walk or run up 2,109 steps during SkyRise Chicago on Nov. 6, a fundraiser for the Rehabilitation Institute of Chicago. ric.convio.net, theskydeck.com, 312-875-9447
While strolling at random (Chicago map in pocket), I reach Daley Plaza, whose many farmers’ market vendors include Brunkow Cheese Co-op in Darlington, southwest of Madison. I part with $3 for “monster cookies” (oatmeal, peanut butter, chocolate) from Rise ’n’ Roll, an Amish bakery near Middlebury, Ind., that began on a house porch in 2001. brunkowcheese.com, 608-776-3716; risenroll.com, 574-825-4032
One alarmingly long line led to a mobile Wendy’s fast food counter, where workers handed out 1,000 free Baconators (double cheeseburgers with bacon). “The ultimate escape to meat lovers trapped in an otherwise kale and bok choy world,” an online press release suggested. wendys.com
Nearly next door is Block 37, an ongoing shopping/dining/entertainment project. While reading a placard for a $25 all-you-can-eat (in two hours) buffet with two beverages (mimosas and more) at Latinicity, a young woman appears with vouchers for free Jarritos, a brand of Mexican soda. “You get a whole bottle,” she promises, so I head two floors up to glimpse the new restaurant. It is a roomy, 10-station food court devoted to made-to-order Latino specialties. blockthirtyseven.com, latinicity.com, 312-795-4444
1:30 p.m. – I open the door to the Chicago Cultural Center and hear applause for free music that is part of the Chicago Jazz Festival, so I climb two stories to Preston Bradley Hall, whose roof is the world’s largest Tiffany stained-glass dome. The building, a public library when it opened in 1897, frequently offers free events and building tours. On now: World Music Festival, ending Sept. 25. cityofchicago.org, 312-744-3316
2 p.m. – I head to the Art Institute of Chicago, where a free trolley stops from January through Labor Day. Why not all year? “It’s like that every year, ma’am,” a Navy Pier receptionist says later, dismissively.
2:30 p.m. – The Navy Pier crowd is sparse but seems content, letting wind muss hairdos while lazily watching sightseeing boats sail in and out. Dark clouds come and go, too, but leave no more than a trickle of rain. In the background is a mix of classic rock and Katy Perry gospel. navypier.com, 800-595-7437
Navy Pier, the longest in the world, juts into Lake Michigan and is a major magnet for tourists, especially families because of the Chicago Children’s Museum, Build-A-Bear Workshop, Funhouse Maze, games and amusement park rides. The new Centennial Wheel has 42 climate-controlled riding compartments and is 50 feet taller than its predecessor, a Ferris wheel now in Branson, Mo.
A stained-glass museum at Navy Pier closed in 2014; only a small gallery of Tiffany windows from the Richard H. Driehaus collection remains. Inside a six-story, domed atrium is the lush, one-acre Crystal Garden, whose foliage includes palm trees.
Also on the six-block-long and 50-acre pier are a beer garden with free music, more restaurants and widespread lakefront views. Under renovation and expansion is Chicago Shakespeare Theatre. chicagoshakes.com, 312-595-5600
4 p.m. – A trolley leaves as I wait to cross Grand Avenue, and the next appears in 20 minutes. I disembark at Grand and Rush streets, then wander contently until sprinkles turn into a light shower. It is a good excuse to duck into Neiman Marcus Last Call, a discount outlet, and 75 percent off signs get my attention.
“Off the lowest price?” I wonder out loud to the woman next to me, who shrugs and says, “I hope so, but that’s still out of my price range.” The dress tag in my hand says $1,450. lastcall.com, 312-973-4990
5 p.m. – I check into Best Western River North because of a $100 rate at priceline.com. That includes free Wi-Fi and a 50 percent off coupon for a drink at Pizzeria Oro, the hotel restaurant. My room is not extraordinary but A-OK in quality, cleanliness. rivernorthhotel.com, 312-467-0800
5:45 p.m. – A quick bite at Osteria La Madia, less than two blocks away, is $5 for a tasty, oblong, four-slice pizza baked in the restaurant’s stone oven and delivered on a wooden plank. A glass of wine is another $5 during this 4:30-6:30 p.m. weekday happy hour. osterialamadia.com, 312-329-0400
6:30 p.m. – The opening reception for colleague Michael Snell’s photo show is well under way, but before I can grab a glass of red, we are whisked into the auditorium of Instituto Cervantes Chicago for the Kansas photographer’s slideshow presentation. michaelcsnell.com
“Colors of Spain,” up until Sept. 26, is one of many Spanish cultural offerings open to the public for free. chicago.cervantes.es, 312-335-1996
9:30 p.m. – I enter Gino’s East River North, around the corner from my hotel, and start heading to the upstairs Comedy Bar for stand-up comedy, only to be told there is only an 8 p.m. show on Thursdays. comedybarchicago.com, 312-836-0499
Around another corner is the unpretentious and compact Blue Chicago, where Shirley Johnson is belting out her heart. The cover charge is $10, and I find a seat at the bar, whose backboard is covered with autographed world currency. Live music happens nightly. bluechicago.com, 312-661-0100
9:30 a.m. Friday – I meet friends for breakfast at AC Hotel Chicago, a Marriott property with a bit of European influence. That includes charcuterie and cheeses at the fine but petite breakfast buffet. $15 for non-guests. marriott.com, 312-981-6600
11:15 a.m. – Among the grand old mansions on Erie Street is Driehaus Museum (named after the same philanthrophist as the Navy Pier gallery). Furnishings and ornate woodwork are a Gilded Age tribute. I peek but don’t have time for a one-hour tour. Admission is $20. driehausmuseum.org, 312-482-8933
11:30 a.m. – I pop in to the fun and funky Freehand Chicago, a hostel-hotel in a revamped 1927 building. Décor in a big lounging area – next to Café Integral – is second-hand, eclectic and cozy. Rates in shared rooms dip to $28 in November. The Penthouse, a suite that sleeps six, is $550 in December. Also in Miami. thefreehand.com, 312-940-3699
12:30 p.m. – A friend and I walk to McCormick and Schmick’s, where we can eat outside and use a gift certificate. Although near the Chicago Riverwalk, our view of city architecture is not too shabby. On the lunch menu are two-course, salad-entrée options for $15. mccormickandschmicks.com, 312-923-7226
2:30 p.m. – Time to scoot back to Union Station for a 3 p.m. Van Galder ride home, with plenty of time to ponder what to do with what I’ve gleaned from this little adventure.