I've reviewed many a Chicago restaurant, park, museum, and event on this blog, but those were one-time or time-sensitive activities that often appealed to Chicagoans themselves, not tourists. Today I'm sharing a several-day plan for both locals and visitors alike - anyone hoping to see a bit of mainstream Chicago attractions while also getting off the beaten path to explore some local flavor.
These activities happened over the course of 5ish days in late April, and moderate weather helped with transportation (lots of walking!) and overall moods (let's linger outside and gaze at this view!). The activities are also geared towards the 21+ crowd, people who mostly enjoy eating, talking, people watching, and chillaxing, and the activities assume there's at least one local in the group to problem solve in the moment and provide a home-away-from-home in the city as base camp.
Day 1: Eat & Laugh & Drink
As a way to ease into Chicago sightseeing, start with a hearty meal and hearty laughs.
Good For: BBQ! And big family get-togethers.
Ambiance: busy, boisterous, organized chaos.
Notes: it's all good here.
Good For: low maintenance laughter.
Ambiance: a little grungy, but a lot of fun.
Notes: visit the bar before taking your seat in the theater - Mike is great!
Day 2: Drink & Play
Check out a few Chicago favorites and entertain yourselves with campfire games.
Notes: Revolution was closed when we tried going, but our original plan was to take a tour, sample some beer, then head somewhere for a relaxed dinner (Kuma's Corner or Honey Butter Fried Chicken). These things are now on our "Next Time" list!
Good For: a change of plans, drinks al fresco, laughing so loud the other tables all stare.
Ambiance: open and relaxed.
Notes: there's no food service on the rooftop, so plan accordingly. (We had a few drinks, then Ubered home for an epic cheese tasting.)
Day 3: Walk & Explore & Eat
Hit up the classic spots in a daylong walking tour.
Blue Line: it doesn't matter which line you choose, but if you're traveling to Chicago, plan to take the L at some point. Travel like you live here!
Field Museum: Jesus and I make it a point to stop at this huge natural history museum whenever free days come around, and off all the museums on Museum Campus, you'll get the biggest bang for your buck here. Our motivation for going in April was to see the Terra Cotta Warrior exhibit - visit before January 8 to check them out!
Giordano's: it's near the Field Museum, and a great option for Chicago deep dish. (See other pizza options here and here.)
Michigan Ave: if it's nice out, take a walk! If it's raining, stop in the many shops that line the street all the way up to Oak Street Beach.
Grant Park: there's plenty to explore within these 319 acres - Millennium Park with the Bean, the Crown Fountain, and Pritzker Pavilion, Buckingham Fountain, and Maggie Daley Park could keep you occupied for several days.
Day 4: Shop til you Drop
Spend some moola.
HIP: Harlem Irving Plaza is just one of the places to go if you have some shopping to do while in Chicago - depending on where you stay you might prefer another mall or shopping center. The HIP features ample parking, prime people watching, and slightly less sales tax than the city proper.
Day 5: Chicago Underground
Avoid the weather (and the crowds) by traveling underground.
Block 37: another shopping option, and also a convenient link from the Blue to the Red Line and/or to Macy's.
Macy's: even if you have nothing to buy, a trip to Macy's includes a view of the Walnut Room, a peek in the Narcissus Room, and unlimited escalator rides.
Chicago Pedway: continue on your underground tour by leaving Macy's through the underground tunnel just past the Starbucks. Word to the wise: parts of this aren't open on the weekends, so plan your underground tour for a weekday.
Cultural Center: bonus freebie! The Cultural Center has rotating art exhibits, so check online to see what's what.
Whew! If you survive all this, congratulations. I hope any visitors enjoy their time in Chicago - check out my other posts for information on other restaurants, museums, and activities!
Extra: Traveling to Philadelphia, Baltimore, San Francisco, or Denver/Boulder? I have a few more suggestions for you!