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What's a good 3-day itinerary for Chicago?

Chicago, United States

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What's a good 3-day itinerary for Chicago?

Day 1 covers the Loop and lakefront, from Cloud Gate at 8:30 AM through the Art Institute and Field Museum. Day 2 heads north to Lincoln Park, Old Town, and Wrigleyville. Day 3 crosses west to Pilsen and the West Loop food corridor. About 28 kilometres of walking total, with CTA L trains connecting neighborhoods.

Day 1 stays below the Chicago River. Start at Millennium Park by 8:30 AM, when the wind off Lake Michigan still has a bite and Cloud Gate reflects the skyline without 200 selfie sticks in the frame. The Bean, as locals call it, went up in 2004 on a 24.5-acre park that took 6 years to finish. Walk south 3 blocks to the Art Institute of Chicago, founded in 1879, and head straight to the Impressionist galleries on the second floor. The Seurat alone is worth the $35 adult ticket. Budget 2 hours. Lunch at Cafecito on Congress Parkway, a Cuban sandwich counter where a pressed cubano runs $11 and the coffee hits harder than you'd expect from a Loop takeout window. Continue south along the lakefront trail to the Field Museum, founded in 1893. The Evolving Earth exhibit on the second floor tends to be quieter than Sue the T. rex in the main hall. Dinner means deep-dish at Lou Malnati's on Wells Street, where a butter-crust sausage pie for two runs about $28. By 8 PM you'll have covered about 9 kilometres on foot.

Day 2 heads to the North Side. Take the Brown Line from the Loop to Armitage, about a 15-minute ride, and start in Lincoln Park by 9:30 AM. The zoo is free, has been since 1868, and the big-cat house smells exactly the way you'd expect, but the paths along the South Pond are worth the detour. Head east to North Avenue Beach by noon. The sand gets warm enough in mid-June to sit on comfortably, and the lifeguard stands are shaped like steamships. Lunch at Twin Anchors on Sedgwick Street in Old Town. They've been slow-smoking ribs since 1932, and the baby backs arrive with a bark that cracks when you pull them apart. A full rack runs about $36. Sinatra used to eat here. Walk it off heading north through Lakeview to Wrigleyville. Even without a Cubs game, the bars around Wrigley Field fill up by 4 PM. Grab a seat at Murphy's Bleachers on Sheffield Avenue for a $7 Old Style and the best people-watching on the North Side.

Day 3 covers the West Side and the far South Side. Start in Pilsen by 10 AM. The Pink Line drops you at 18th Street, and the murals begin within a block. 16th Street between Halsted and Ashland is the densest stretch. Breakfast at Carnitas Don Pedro on West 18th, where a half-pound of carnitas with two handmade tortillas, raw onion, and salsa verde costs $9. The pork is braised for 8 hours and falls apart under a fork. From Pilsen, take the L north to the West Loop, where Randolph Street between Halsted and Racine holds more restaurants per block than any other corridor in the city. Girl & The Goat at 809 W Randolph still draws a crowd 16 years in. Walk 2 blocks south to Fulton Market, where the old meatpacking warehouses smell faintly of cold concrete and now hold galleries and design studios. If energy holds, take the 6 bus south to Hyde Park for the Museum of Science and Industry, founded in 1933. The U-505 submarine capture exhibit on the lower level is the best single room in any Chicago museum.

A 3-day CTA pass costs $20 and covers every L train and bus route. Buy one at any station kiosk at O'Hare or Midway. The Blue Line runs from O'Hare to the Loop in about 45 minutes for $5. Mid-June temperatures sit around 22 to 27 degrees Celsius, but the lake wind drops the feel by 3 or 4 degrees. Bring a layer for the lakefront. Chicago's grid runs on one rule. State Street divides east from west, Madison Street divides north from south, and 8 blocks equal one mile.

28 km total distance covered

Walking + transit across the three-day route.

Day one

  1. 8:30 AM

    Walk through Millennium Park to Cloud Gate. The Bean reflects the skyline clean at this hour, before tour groups arrive around 10. The park opened in 2004 and covers 24.5 acres.

    The Loop
  2. 10:30 AM

    Art Institute of Chicago, founded 1879. Head straight to the second-floor Impressionist galleries. Budget 2 hours for Seurat, Monet, and the Thorne Miniature Rooms. Adult ticket $35.

    The Loop
  3. 12:30 PM

    Lunch at Cafecito on Congress Parkway. Pressed cubano sandwich, $11. Cuban coffee strong enough to reset your afternoon.

    The Loop
  4. 2 PM

    Walk south along the lakefront trail to Museum Campus. About 2.5 kilometres, flat, with the skyline behind you and the lake smell thickening as you go.

    Near South Side
  5. 2:30 PM

    Field Museum of Natural History, founded 1893. Sue the T. rex is in the main hall. The Evolving Earth exhibit on the second floor is quieter and better.

    Museum Campus
  6. 6 PM

    Deep-dish pizza at Lou Malnati's on Wells Street. Butter-crust sausage pie for two, about $28. Expect a 30-minute wait without a reservation.

    River North

Day two

  1. 9:30 AM

    Lincoln Park Zoo, free admission since 1868. The big-cat house and the South Pond paths are the highlights. Budget 90 minutes.

    Lincoln Park
  2. 12 PM

    Walk east to North Avenue Beach, about 1.5 kilometres from the zoo. The lifeguard stands are shaped like steamships. Sit on the sand if mid-June warmth cooperates.

    Gold Coast
  3. 1 PM

    Lunch at Twin Anchors on Sedgwick Street. Baby back ribs slow-smoked since 1932. Full rack about $36. Sinatra used to eat here.

    Old Town
  4. 3 PM

    Walk north through Lakeview toward Wrigleyville, about 3 kilometres. The neighborhood shifts from brownstones to sports bars across 20 blocks.

    Lakeview
  5. 4:30 PM

    Murphy's Bleachers on Sheffield Avenue, across from Wrigley Field. $7 Old Style beer and good people-watching even without a Cubs game.

    Wrigleyville
  6. 7 PM

    Dinner at Crisp on Broadway. Korean-style fried chicken wings. The Seoul Sassy combo runs about $15.

    Lakeview

Day three

  1. 10 AM

    Pink Line to 18th Street station. Walk the Pilsen murals along 16th Street between Halsted and Ashland, the densest stretch of public art in Chicago.

    Pilsen
  2. 10:30 AM

    Breakfast at Carnitas Don Pedro on West 18th Street. Half-pound carnitas plate with handmade tortillas and salsa verde, $9. The pork is braised for 8 hours.

    Pilsen
  3. 12 PM

    L train north to the West Loop. Walk Randolph Street between Halsted and Racine, the densest restaurant block in the city.

    West Loop
  4. 1 PM

    Lunch at Girl & The Goat, 809 W Randolph. Reservations recommended. The wood-oven roasted pig face is the signature dish.

    West Loop
  5. 2:30 PM

    Walk south to Fulton Market. Former meatpacking district turned gallery and design corridor. The old warehouse loading docks still line the sidewalks.

    Fulton Market
  6. 4 PM

    Number 6 bus south to Hyde Park. Museum of Science and Industry, founded 1933. The U-505 submarine capture exhibit on the lower level is the single best room in any Chicago museum.

    Hyde Park
  7. 7 PM

    Dinner at Valois cafeteria on 53rd Street. Counter-service comfort food under the slogan 'See Your Food.' Obama ate here regularly as a senator. Meatloaf plate about $12.

    Hyde Park

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