8:30 AMLou Mitchell's
Food & Drink4.6$
Diner on old Route 66. Free donut holes while you wait — the wait is part of it.
Like this trip? Make it yours — change anything, add your own places.
Planning board
Est. budget ~$205 / person1
Day 1 · Fri, Sep 18
7 stops5.1 km9h 30m planned~66 min walk~$85
8:30 AM
9:45 AMThe Art Institute of Chicago
Activities4.8
Go straight upstairs to the Impressionists, then Nighthawks. Two hours is the honest minimum.
12:00 PMMillennium Park
Activities4.8
Cloud Gate is five minutes of photos. The Lurie Garden behind it is the part people miss.
12:50 PMThe Gage
Food & Drink4.6
Irish-leaning gastropub across from Millennium Park — the fast, good lunch before the 2:15 cruise dock two blocks north.
2:15 PMChicago Architecture Center
Activities4.7
The river cruise is the single best thing in the city. Book ahead, sit on the left.
4:00 PMChicago Riverwalk
Activities4.8
Come off the cruise and walk the same bridges at eye level. Drink stop at the wine terraces on the way west.
7:00 PMGirl & The Goat
Food & Drink4.7$$$
Book the moment you have dates. Wood-fired everything; the pig face is not a dare, it's the order.
2
Day 2 · Sat, Sep 19
7 stops22.4 km9h 15m planned~291 min walk~$120
9:00 AMBang Bang Pie & Biscuits
Food & Drink4.7$
Biscuit, jam bar, coffee on the patio. Low-key start before a walking day.
10:00 AMThe 606
Activities4.8
Climb up at California, two blocks from Bang Bang, and walk the old rail line east — come down at Damen and Big Star is on the corner.
11:30 AMBig Star
Food & Drink4.4$$
Tacos al pastor and whiskey on a big patio. Counter service, no reservations.
1:45 PMWillis Tower Skydeck
Activities4.6
The Ledge — glass boxes 103 floors over Wacker. Buy the timed ticket the day before; the Saturday walk-up line is brutal.
3:30 PMThe Magnificent Mile
Activities
Michigan Avenue's shopping mile, with the old Water Tower halfway up. Less about buying, more about the canyon of it.
5:30 PMLou Malnati's Pizzeria
Food & Drink4.4$$
Deep dish takes 45 minutes to bake — order it the second you sit down.
9:00 PMThe Green Mill
Other4.3$$
Al Capone's old bar, still a working jazz club. Cash at the door, quiet during sets.
3
Day 3 · Sun, Sep 20
5 stops7.2 km7h 15m planned~94 min walk
9:30 AMLincoln Park Zoo
Activities4.6
Free zoo in the middle of the city. In fifteen minutes you can be at the lions.
11:15 AMNorth Avenue Beach
Activities4.6
The skyline postcard shot, from sand. Walk the lakefront trail south and watch the towers grow.
12:45 PMPortillo's
Food & Drink4.4
Chicago dog — dragged through the garden, no ketchup, don't ask. Split a chocolate cake shake.
2:15 PMNavy Pier
Activities4.6
Touristy and worth it once. The Centennial Wheel at dusk gives you the skyline from the water.
5:30 PMThe Purple Pig
Food & Drink4.6
Mediterranean small plates just off the Mag Mile — an easy walk from Navy Pier and the right Sunday-night close to the trip.