UrbanPicnics

United States

Chicago

Chicago has twenty-six miles of continuous public lakefront and a food culture built on things you eat wrapped in paper while standing up. The combination is the best argument for eating outdoors in any American city.

5 places to sit · 10 places to buy food · checked 2026-09-14

Green markers are the picnic spots. Amber ones are where to buy the food. Every place below also links straight to Google Maps for walking directions.

Before you go

  • The lakefront is windy and about ten degrees cooler than the Loop. Bring a layer even in July.
  • Italian beef is served wet, with the roll dunked in gravy. It does not survive a long walk. Eat it close to where you bought it or order it dry.
  • Alcohol is not permitted in Chicago parks or on the beaches, and it is enforced.

Chicago Riverwalk

The Loop

A mile and a half of public path cut in below street level along the south bank of the river, so the traffic noise disappears and you're left looking straight up at the Wrigley Building and the Marina City corncobs.

Where to sit
Tiered steps down to the water, floating gardens, and benches the whole way.
Open
6am–11pm, roughly April to October. Quieter in winter.

Walking directions to Chicago Riverwalk

Pick up food first

  1. XOCO

    $$

    Wood-oven tortas, caldos and churros

    Rick Bayless's counter-service place. The shortrib torta is the one. Closed two days a week.

    10 min walk Tue–Sat from 11am (Sat from 10.30am). Closed Sun & Mon.

    65 W Illinois St, 60654 · Directions

  2. Mr. Beef

    $

    Italian beef, hot and wet, with giardiniera

    The one The Bear is based on. Order it dry if you're walking to the river, or you'll be wearing it.

    21 min walk Mon–Sat 10am–4pm. Closed Sunday.

    666 N Orleans St, 60654 · Directions

  3. Cafecito

    $

    Pressed Cuban sandwiches and strong coffee

    South end of the Loop. Around $10 for a sandwich that will genuinely do for two people.

    22 min walk Mon–Fri 8am–8pm, weekends 8am–6pm

    26 E Congress Pkwy, 60605 · Directions

Milton Lee Olive Park

Streeterville

A small peninsula of lawn and fountains behind the water filtration plant, next to Ohio Street Beach. The skyline view is the postcard one and, because there is no obvious reason to walk out here, it is usually half empty.

Where to sit
Open lawn, benches and a small beach. Very exposed to the wind.
Open
7am–8pm.

Walking directions to Milton Lee Olive Park

Pick up food first

  1. XOCO

    $$

    Tortas and caldos to go

    Pick up on your way east — it's a 25-minute walk down Illinois and past Navy Pier, and the torta holds its heat.

    26 min walk Tue–Sat. Closed Sun & Mon.

    65 W Illinois St, 60654 · Directions

The 606 at Damen

Wicker Park / Bucktown

An old elevated freight line turned into a planted trail running nearly three miles west through the North Side. You're one storey above the street, eye-level with the treetops and people's second-floor windows.

Where to sit
Benches and small planted plazas at each access ramp. Sunset views west along the line.
Open
6am–11pm.

Walking directions to The 606 at Damen

Pick up food first

  1. Big Star

    $$

    Tacos al pastor, fish tacos, elotes

    In a converted 1940s gas station. There's a dedicated takeaway window, which is much faster than the patio.

    7 min walk Daily from 11am (11.30am weekdays)

    1531 N Damen Ave, 60622 · Directions

  2. Papa's Cache Sabroso

    $

    Jibarito — a sandwich using flattened fried plantains instead of bread — and rotisserie chicken

    The jibarito was invented in Chicago's Puerto Rican neighbourhoods. This is one of the best versions.

    25 min walk Mon–Sat from 11.30am. Closed Sunday.

    2517 W Division St, 60622 · Directions

Promontory Point

Hyde Park

A man-made headland pushing out into Lake Michigan, ringed with limestone blocks that step down into the water. Look north and the entire skyline sits on the horizon five miles away. Locals call it The Point and guard it fiercely.

Where to sit
Grass under old trees, limestone blocks at the water's edge, fire pits if you get there early.
Open
6am–11pm.

Walking directions to Promontory Point

Pick up food first

  1. Valois

    $$

    Cafeteria-line American food: steam-table roasts, omelettes, pancakes

    Cash only. Open since 1921 and a Hyde Park institution. Point at what you want as you go down the line.

    16 min walk Daily 6am–3pm

    1518 E 53rd St, 60615 · Directions

  2. Medici on 57th

    $

    Sandwiches, pizza and a bakery counter next door

    The bakery next door does the bread. A good stop if you're walking up from the Museum of Science and Industry.

    23 min walk Daily 8am–8pm (later Fri & Sat)

    1327 E 57th St, 60637 · Directions

Maggie Daley Park

The Loop

Twenty acres of engineered landscape on top of a car park: rolling hills, a quarter-mile skating ribbon, climbing walls, and a playground good enough that adults visit without children. Millennium Park is over the bridge.

Where to sit
Grass on the artificial hills, benches, and the wooded picnic grove on the east side.
Open
6am–10pm.

Walking directions to Maggie Daley Park

Pick up food first

  1. Cafecito

    $

    Cuban sandwiches, pressed to order

    Ten minutes south through Grant Park. The sandwiches hold up well pressed and wrapped.

    15 min walk Mon–Fri 8am–8pm, weekends 8am–6pm

    26 E Congress Pkwy, 60605 · Directions

  2. XOCO

    $$

    Tortas, soups and churros

    North across the river. Worth the walk if you're in the park on a weekday.

    21 min walk Tue–Sat. Closed Sun & Mon.

    65 W Illinois St, 60654 · Directions

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