Chicago rose from the ashes of the Great Fire of 1871 to become a living gallery of innovation—steel-frame skyscrapers, prairie-style design, and bold public art that anchors a world-class skyline. The Loop, the compact heart of the city, hums with theater marquees, historic towers, and L trains tracing curves above century-old streets.

From the Art Institute’s masterpieces to Millennium Park’s public art, from the Riverwalk to the Lake Michigan shoreline, this itinerary spotlights the best things to do in Chicago for first-timers and repeat visitors. Architecture is the throughline, but cuisine is the chorus—Italian beef, Chicago dogs, deep-dish pizza, and a flourishing chef-driven scene.

Expect walkable days, quick transit hops, and memorable viewpoints. Pack layers (the Windy City earns its nickname), reserve top attractions in advance, and consider a CTA pass for easy rides. Come hungry, bring a camera, and let the Loop be your launchpad to a quintessential Chicago city break.

Chicago

The Loop is Chicago’s living scrapbook: historic theaters, the glittering river canyon, and parks that roll east to Lake Michigan. Trains skim overhead, while street-level cafes, cocktail dens, and classic taverns tell stories of the city’s energy and grit.

• Top sights: Art Institute of Chicago, Millennium Park & Cloud Gate, Chicago Riverwalk, Willis Tower Skydeck, Chicago Cultural Center, State Street shopping.
• Food & drink: Deep-dish at Lou Malnati’s or Pizano’s; Italian beef at Luke’s; modern Midwestern at The Dearborn; historic steins at The Berghoff; cocktails at Vol. 39 and Cindy’s Rooftop.
• Fun facts: The Loop’s elevated tracks gave the neighborhood its name; Chicago pioneered the skyscraper; the river famously flowed backward after a monumental engineering project in 1900.

Where to stay (Loop + nearby): For central access to museums, architecture tours, and theaters, base yourself in the Loop or just across the river in River North.

• Apartment-style stays: Browse options on VRBO Chicago—ideal for groups or families wanting kitchens and lounge space.
• Hotels across budgets: Compare central stays on Hotels.com Chicago—filter by walkability to Millennium Park and the Riverwalk.

Getting to Chicago: Fly into O’Hare (ORD) or Midway (MDW). Compare fares on Trip.com flights or Kiwi.com (typical domestic roundtrips run ~$120–$350 depending on season). From ORD, take the CTA Blue Line (~45–50 minutes to the Loop). From MDW, the Orange Line takes ~25–30 minutes.

Day 1: Arrival, Millennium Park, and the Riverwalk

Afternoon: Arrive and check in. Stretch your legs on the Chicago Riverwalk, ducking into tiny bridgeside museums, public art nooks, and river-level patios. Grab a sweet pick-me-up at Goddess and the Baker (Loop) or a maple bacon donut at Do-Rite Donuts & Chicken.

Evening: Wander to Millennium Park for Cloud Gate (a.k.a. “The Bean”) and Crown Fountain’s twin video towers. For dinner, book The Dearborn (modern Midwestern—short rib stroganoff, Lake Erie walleye) or The Gage (game sausage, scotch eggs, deep beer list) on Michigan Avenue.

Night: Toast your first night with skyline views at Cindy’s Rooftop (Chicago Athletic Association) overlooking the park. If you prefer an intimate library vibe, slip into Vol. 39 at the Kimpton Gray for martinis and a polished, old-Chicago feel.

Day 2: Art and Architecture—Masterpieces to the River Canyon

Morning: Fuel up at Wildberry Pancakes & Cafe (blueberry danish pancakes, chilaquiles) steps from Millennium Park. Spend the morning at the Art Institute of Chicago, home to Grant Wood’s American Gothic, Seurat’s A Sunday on La Grande Jatte, and a superb Impressionist collection (plan 2–3 hours; timed entry recommended).

Afternoon: See the skyline from the water on a celebrated architecture cruise. We like the 90-minute deep dive:

Chicago River 90-Minute Architecture Tour (from ~$45–$55; departures throughout the day)

Between boats, graze at Revival Food Hall—a chef-driven lineup under one roof. Try Smoque BBQ (pulled pork, brisket), Lito’s Empanadas, The Budlong Hot Chicken, or Aloha Poke.

Evening: Time sunset at the city’s highest classic viewpoint:

Skydeck - Willis Tower Admission (timed entry; The Ledge glass boxes are a thrill—photos at golden hour are spectacular)

Cap the night with deep-dish: Lou Malnati’s (buttery crust, sausage patty under a fresh tomato blanket) or Pizano’s for a slightly lighter, crackly crust. For post-pizza blues, head to Buddy Guy’s Legends in the South Loop for live sets most nights.

Day 3: Chicago Bites, Museum Campus, and a Lake Michigan Sunset

Morning: Coffee at Dollop Coffee Co. or a honey latte at Hero Coffee Bar. Then dive into a guided tasting-and-history stroll—ideal for first-timers to learn the city’s flavor canon:

Chicago Favorites Ultimate Food and Walking Tour (classic pizza, hot dog with the “garden on top,” brownies—allow ~3 hours)

Afternoon: Stroll the Lakefront Trail and head to the Museum Campus for an optional museum stop. The Field Museum is a favorite for SUE the T. rex, ancient Egypt, and gems—perfect if weather turns. Alternatively, browse the Chicago Cultural Center (free) for exhibitions under the world’s largest Tiffany dome.

Evening: End the day on the water as the skyline lights flicker on:

Lake Michigan Sunset Cruise in Chicago (a serene, photogenic finale; lock passage from the river to the lake is a bonus highlight)

For dinner, cross the river to The Purple Pig (Mediterranean small plates—milk-braised pork shoulder, whipped feta, fried olives) or stay near the Loop for a classic steakhouse fix at Prime & Provisions on Wacker Drive.

Day 4: Culture Fix, State Street, and Farewell Bites

Morning: Ease into the day at Beatrix Market (healthy grab-and-go, strong coffee) or Yolk – South Loop (scrambles, lemon blueberry pancakes). Walk the whimsical footbridges of Maggie Daley Park or duck into the Chicago Cultural Center if you missed it—its beaux-arts interiors are a photographer’s dream.

Afternoon: Last-minute shopping along State Street and a final bite: try Luke’s Italian Beef on Jackson (dipped, with sweet or hot peppers) or a Chicago-style dog at Portillo’s (River North is a quick walk). Depart in the afternoon—Orange Line to MDW (~25–30 minutes) or Blue Line to ORD (~45–50 minutes). If time allows and skies are clear, consider a final viewpoint at 875 N Michigan (formerly Hancock) for another lake-meets-city panorama.

Evening: Fly home with a camera roll full of river reflections and skyline sunsets. For the next visit, pencil in neighborhood day trips—West Loop dining, Lincoln Park’s conservatory, or a Wrigleyville game day.

Local tips: The CTA 1-day, 3-day, and 7-day passes offer great value if you’re riding often. Winters are cold—pack windproof layers; summers are glorious but bring sunscreen for boat days. Sales tax in the city is among the highest in the U.S.—factor it into dining and shopping budgets.

Optional swaps and add-ons: If you crave more views, the 360 CHICAGO Observation Deck on the Magnificent Mile offers a lake-forward perspective and an optional TILT experience. Theater fans should check Broadway In Chicago venues (CIBC, Nederlander, Cadillac Palace) for touring productions and last-minute tickets.

Getting here or back: Compare flight options on Trip.com or Kiwi.com for flexible times into ORD/MDW—early arrivals and late departures stretch your sightseeing.

Summary: Four days in the Chicago Loop lets you sample the city’s signature trio: world-class art, soaring architecture, and a comfort-food canon with real character. With river cruises, sky-high viewpoints, and easy transit, it’s an urban getaway that’s both efficient and unforgettable.