See Cloud Gate (The Bean)Must-See SightsThe Bean is the obvious first stop in Millennium Park — a massive mirror-polished sculpture that reflects the skyline and everyone around it. Free, always open, usually busy on weekends.0 Add to listSee Cloud Gate (The Bean)Must-See SightsThe Bean is the obvious first stop in Millennium Park — a massive mirror-polished sculpture that reflects the skyline and everyone around it. Free, always open, usually busy on weekends.0 Add to list
Step onto the Willis Tower SkydeckMust-See SightsPaidThe Willis Tower Skydeck puts you on the 103rd floor with glass-box ledges that extend out over the street. Ticketed, can be a queue — booking ahead is worth it.0 Add to listStep onto the Willis Tower SkydeckMust-See SightsPaidThe Willis Tower Skydeck puts you on the 103rd floor with glass-box ledges that extend out over the street. Ticketed, can be a queue — booking ahead is worth it.0 Add to list
Ride the Navy Pier Ferris wheelMust-See SightsWith KidsPaidNavy Pier is busy and commercial, but the Centennial Wheel gives decent lake views and it's an easy waterfront stop. Worth an hour, especially with kids.0 Add to listRide the Navy Pier Ferris wheelMust-See SightsWith KidsPaidNavy Pier is busy and commercial, but the Centennial Wheel gives decent lake views and it's an easy waterfront stop. Worth an hour, especially with kids.0 Add to list
Visit the Art Institute of ChicagoMust-See SightsPaidThe Art Institute of Chicago is one of the better art museums in the US — strong on Impressionism and American art. The bronze lions out front are a classic photo stop. Budget two to three hours.0 Add to listVisit the Art Institute of ChicagoMust-See SightsPaidThe Art Institute of Chicago is one of the better art museums in the US — strong on Impressionism and American art. The bronze lions out front are a classic photo stop. Budget two to three hours.0 Add to list
Walk the Chicago RiverwalkMust-See SightsThe Chicago Riverwalk is a flat, walkable promenade along the main branch of the river — good for a stroll and for looking up at the architecture from street level. Free and easy.0 Add to listWalk the Chicago RiverwalkMust-See SightsThe Chicago Riverwalk is a flat, walkable promenade along the main branch of the river — good for a stroll and for looking up at the architecture from street level. Free and easy.0 Add to list
Take an architecture river cruiseMust-See SightsPaid · SummerThe Chicago Architecture Foundation river cruise is probably the best way to understand the skyline. Guides cover the history and style of dozens of buildings in about 90 minutes. Book ahead in summer.0 Add to listTake an architecture river cruiseMust-See SightsPaid · SummerThe Chicago Architecture Foundation river cruise is probably the best way to understand the skyline. Guides cover the history and style of dozens of buildings in about 90 minutes. Book ahead in summer.0 Add to list
Relax in Millennium ParkMust-See SightsWith KidsMillennium Park is free, central and easy — the Bean, Crown Fountain and Pritzker Pavilion are all here. Good for a couple of hours, especially with kids.0 Add to listRelax in Millennium ParkMust-See SightsWith KidsMillennium Park is free, central and easy — the Bean, Crown Fountain and Pritzker Pavilion are all here. Good for a couple of hours, especially with kids.0 Add to list
Meet SUE at the Field MuseumMust-See SightsWith KidsPaidThe Field Museum has one of the largest T. rex skeletons ever found, plus strong exhibits on Egypt and ancient cultures. Budget two to three hours. Ticketed.0 Add to listMeet SUE at the Field MuseumMust-See SightsWith KidsPaidThe Field Museum has one of the largest T. rex skeletons ever found, plus strong exhibits on Egypt and ancient cultures. Budget two to three hours. Ticketed.0 Add to list
Order a Malort Shot at a Chicago Dive BarLocal FoodLocal RitualsMalort is a Chicago bitter liqueur that tastes genuinely awful — ordering one at a dive bar is a rite of passage. Order it with a cheap Old Style back and don't make any plans afterward.0 Add to listOrder a Malort Shot at a Chicago Dive BarLocal FoodLocal RitualsMalort is a Chicago bitter liqueur that tastes genuinely awful — ordering one at a dive bar is a rite of passage. Order it with a cheap Old Style back and don't make any plans afterward.0 Add to list
Find the Bronze Poo Fountain in BucktownFun Side QuestsJerzy Kenar's bronze poo fountain at 1001 N Wolcott in Bucktown is exactly what it sounds like — an artist's very pointed plea to dog owners. Yes, it actually runs water. Quick stop, free.0 Add to listFind the Bronze Poo Fountain in BucktownFun Side QuestsJerzy Kenar's bronze poo fountain at 1001 N Wolcott in Bucktown is exactly what it sounds like — an artist's very pointed plea to dog owners. Yes, it actually runs water. Quick stop, free.0 Add to list
Visit the Busy Beaver Button MuseumFun Side QuestsThe Busy Beaver Button Museum in Logan Square is a free, tiny storefront dedicated to pinback buttons and their history. Takes about 20 minutes and the collection is genuinely odd.0 Add to listVisit the Busy Beaver Button MuseumFun Side QuestsThe Busy Beaver Button Museum in Logan Square is a free, tiny storefront dedicated to pinback buttons and their history. Takes about 20 minutes and the collection is genuinely odd.0 Add to list
Find the Stained-Glass Windows in the PedwayFun Side QuestsThe Pedway is Chicago's underground tunnel network connecting downtown buildings. Near the Macy's entrance at Randolph and Wabash, there are backlit Victorian stained-glass windows that most people walk straight past.0 Add to listFind the Stained-Glass Windows in the PedwayFun Side QuestsThe Pedway is Chicago's underground tunnel network connecting downtown buildings. Near the Macy's entrance at Randolph and Wabash, there are backlit Victorian stained-glass windows that most people walk straight past.0 Add to list
Find the Tin Man in Lincoln ParkFun Side QuestsWith KidsOz Park in Lincoln Park has four Wizard of Oz statues scattered around it — L. Frank Baum grew up nearby. The Tin Man is welded from old car parts. Easy family stop, free.0 Add to listFind the Tin Man in Lincoln ParkFun Side QuestsWith KidsOz Park in Lincoln Park has four Wizard of Oz statues scattered around it — L. Frank Baum grew up nearby. The Tin Man is welded from old car parts. Easy family stop, free.0 Add to list
Dig Through the Zines at Quimby'sFun Side QuestsQuimby's on North Avenue in Wicker Park stocks zines, comics and unusual small-press books. Worth a browse if you like that kind of thing — the buyer leans toward the strange.0 Add to listDig Through the Zines at Quimby'sFun Side QuestsQuimby's on North Avenue in Wicker Park stocks zines, comics and unusual small-press books. Worth a browse if you like that kind of thing — the buyer leans toward the strange.0 Add to list
Eat Smoked Fish in a Parked CarLocal FoodLocal RitualsCalumet Fisheries is a one-room shack on the far south side that's been smoking fish since 1928. No seats — order the smoked shrimp and eat in your car by the bridge. James Beard-awarded, worth the drive.0 Add to listEat Smoked Fish in a Parked CarLocal FoodLocal RitualsCalumet Fisheries is a one-room shack on the far south side that's been smoking fish since 1928. No seats — order the smoked shrimp and eat in your car by the bridge. James Beard-awarded, worth the drive.0 Add to list
Slip Into the Fern Room at Garfield Park ConservatoryFun Side QuestsWinterThe Fern Room at Garfield Park Conservatory is a free indoor tropical space with a hidden lagoon and ancient-feeling ferns. A genuinely good winter escape from the cold.0 Add to listSlip Into the Fern Room at Garfield Park ConservatoryFun Side QuestsWinterThe Fern Room at Garfield Park Conservatory is a free indoor tropical space with a hidden lagoon and ancient-feeling ferns. A genuinely good winter escape from the cold.0 Add to list
Order a Volcano at a 1964 Tiki BarLocal FoodCheck AccessHala Kahiki in River Grove is a proper 1960s tiki bar that's been running since 1964 with over 100 tropical drinks. No beer on tap, cash preferred — call ahead to check hours before the drive out.0 Add to listOrder a Volcano at a 1964 Tiki BarLocal FoodCheck AccessHala Kahiki in River Grove is a proper 1960s tiki bar that's been running since 1964 with over 100 tropical drinks. No beer on tap, cash preferred — call ahead to check hours before the drive out.0 Add to list
Visit the Nine-Sided Baha'i Temple in WilmetteFun Side QuestsThe Baha'i House of Worship in Wilmette is a free nine-sided white stone building open to anyone. It's quiet, genuinely beautiful inside, and about 45 minutes on the Red Line from downtown.0 Add to listVisit the Nine-Sided Baha'i Temple in WilmetteFun Side QuestsThe Baha'i House of Worship in Wilmette is a free nine-sided white stone building open to anyone. It's quiet, genuinely beautiful inside, and about 45 minutes on the Red Line from downtown.0 Add to list
Run the Lakefront Trail before the bikes wake upActiveLocal RitualsThe 18-mile Lakefront Trail along Lake Michigan is best early morning before cyclists take over. The stretch from Montrose south gives good skyline views and usually a lake breeze.0 Add to listRun the Lakefront Trail before the bikes wake upActiveLocal RitualsThe 18-mile Lakefront Trail along Lake Michigan is best early morning before cyclists take over. The stretch from Montrose south gives good skyline views and usually a lake breeze.0 Add to list
Jog the 606 Elevated TrailActiveLocal RitualsThe 606 is a 2.7-mile elevated trail built on an old freight rail line above the northwest side. Good for a run or walk above street level, with murals and treetop views. Drops into Logan Square at the west end.0 Add to listJog the 606 Elevated TrailActiveLocal RitualsThe 606 is a 2.7-mile elevated trail built on an old freight rail line above the northwest side. Good for a run or walk above street level, with murals and treetop views. Drops into Logan Square at the west end.0 Add to list
Stand in the Crown Fountain spray at Millennium ParkFun Side QuestsWith KidsSummerCrown Fountain in Millennium Park has two glass towers projecting giant faces that periodically squirt water into a shallow pool. Kids love it. Free, and the soaking is reliably funny.0 Add to listStand in the Crown Fountain spray at Millennium ParkFun Side QuestsWith KidsSummerCrown Fountain in Millennium Park has two glass towers projecting giant faces that periodically squirt water into a shallow pool. Kids love it. Free, and the soaking is reliably funny.0 Add to list
Explore Maggie Daley Park's Slide Crater playgroundFun Side QuestsWith KidsMaggie Daley Park's free Play Garden has a big multi-level playground with nets, a pirate ship and a slide tower. Good for letting kids run while adults sit with a view of the skyline.0 Add to listExplore Maggie Daley Park's Slide Crater playgroundFun Side QuestsWith KidsMaggie Daley Park's free Play Garden has a big multi-level playground with nets, a pirate ship and a slide tower. Good for letting kids run while adults sit with a view of the skyline.0 Add to list
Pet a goat at the free zoo's barnyardActiveWith KidsLincoln Park Zoo is fully free every day. Farm-in-the-Zoo is a working barnyard tucked inside with goats, ponies and cows. Easy half-day stop right in the city.0 Add to listPet a goat at the free zoo's barnyardActiveWith KidsLincoln Park Zoo is fully free every day. Farm-in-the-Zoo is a working barnyard tucked inside with goats, ponies and cows. Easy half-day stop right in the city.0 Add to list
