Chicago rises from the prairies as a city of reinvention—rebuilt after the Great Fire of 1871, vaulted skyward by steel-frame skyscrapers, and shaped by waves of immigrants whose food and music still soundtrack its streets. It’s the birthplace of the modern skyline, the blues, the house music movement, and yes, the Cubs’ lovable drama.

Today, the Windy City balances grit and grace: avant‑garde architecture, Lake Michigan’s beachy serenity, and neighborhoods with distinct flavors, from dim sum in Chinatown to tacos in Pilsen and Michelin‑starred innovation in the West Loop. Art lovers, design nerds, sports fanatics, and pizza partisans all find their corner.

Practical notes: Chicago is walkable downtown, and the CTA trains and buses make cross‑city travel straightforward (1‑Day CTA pass ~$5; 3‑Day ~$15; 7‑Day ~$20). Winters are bracing; spring and fall are glorious; summers brim with festivals. Book popular restaurants and observation decks in advance, especially on weekends and at sunset.

Chicago

Look up to read the city—Louis Sullivan’s ornament, Frank Lloyd Wright’s geometry, Mies van der Rohe’s “less is more,” and contemporary glass towers catching lake light. The Riverwalk turns architecture into an open‑air gallery, while the Lakefront Trail strings beaches, parks, and skyline views together like a ribbon.

• Top sights: Millennium Park and the Art Institute, the Museum Campus (Field, Shedd, Adler), Wrigley Field, Lincoln Park Zoo, Garfield Park Conservatory, Hyde Park’s University of Chicago and Robie House, the Magnificent Mile.
• Essential tastes: deep‑dish (Pequod’s, Lou Malnati’s), Chicago‑style hot dogs (Portillo’s, Superdawg), Italian beef (Johnnie’s, Al’s), West Loop dining (Girl & the Goat, Monteverde, Avec), pastries and coffee (Kasama, Intelligentsia, Dark Matter).
• Where to stay: River North and the Loop for first-timers; West Loop and Fulton Market for dining; Lincoln Park or Wicker Park for leafy, neighborhood vibes.

Getting to Chicago: Fly into O’Hare (ORD) or Midway (MDW). Search fares on Trip.com flights or Kiwi.com flights. Typical nonstop times: NYC ~2.5 hrs, Dallas ~2.25 hrs, LA ~4 hrs. Economy fares often range $120–$350 roundtrip from major US hubs depending on season and advance purchase.

Airport to downtown: From ORD, CTA Blue Line to the Loop (~45 min; ~$5). From MDW, Orange Line (~25 min; ~$2.50). Rideshares take 30–60 min depending on traffic.

Where to stay (book with our partners):

• Browse vacation rentals on VRBO Chicago or hotels on Hotels.com Chicago.
• Favorites: The Peninsula Chicago (elegant, indoor pool, top-tier spa), Freehand Chicago (stylish, social, great value), Embassy Suites by Hilton Chicago Downtown Magnificent Mile (suites, breakfast included, family-friendly).

Day 1: Arrival, Riverwalk, and a Classic First Bite

Afternoon: Arrive and check in. Shake off the flight with a relaxing stroll along the Chicago Riverwalk from Michigan Avenue to Lake Street—watch tour boats glide by and study the facades you’ll learn more about later.

Evening: Welcome dinner downtown. For deep‑dish, go to Lou Malnati’s (River North) for a buttery crust and tangy sauce, or Gino’s East for cornmeal crust and retro graffiti walls. Prefer something lighter? Ema serves bright Mediterranean spreads and tender kebabs; The Gage opposite Millennium Park does elevated pub fare (venison burger, Scotch eggs). Cap the night with skyline views at LondonHouse Rooftop—order the Old Fashioned with a lake breeze.

Day 2: Millennium Park, Art Institute, and the Chicago River Architecture Tour

Morning: Coffee at Intelligentsia (Millennium Park) or Hero Coffee Bar (look for the ivy‑wrapped alley). Walk Millennium Park: Cloud Gate (aka “The Bean”), Crown Fountain, and the Frank Gehry‑designed Pritzker Pavilion. If any fencing remains around Cloud Gate due to improvements, admire from the perimeter and continue through the Lurie Garden.

Afternoon: Explore the Art Institute of Chicago—home to Seurat’s “A Sunday on La Grande Jatte,” Grant Wood’s “American Gothic,” and a stunning Modern Wing. Lunch nearby at Revival Food Hall (local vendors under one roof—try Smoque BBQ’s brisket or a veggie bibimbap bowl) or The Dearborn for contemporary Midwestern comfort food.

Evening: See the skyline from the water on the Chicago River 90-Minute Architecture Tour—a local rite of passage packed with stories about Burnham, Wright, and modernist icons.

Finish in the West Loop: book Girl & the Goat (bold, shareable plates), Monteverde (hand‑rolled pastas like the cacio whey pepe), or Avec (legendary chorizo‑stuffed dates). For a nightcap, try The Darling (cocktails and cabaret vibes) or The Violet Hour in Wicker Park for classic, candlelit mixology.

Day 3: Museum Campus Deep Dive and North Side Nights

Morning: Head to the Museum Campus on the lakefront. Start with the Field Museum of Natural History to meet SUE the T. rex and explore Egypt, evolving planet exhibits, and the glittering Hall of Gems.

Fuel up before or after with coffee and a pastry at Spoke & Bird (South Loop) or Dollop Coffee Co. (Printer’s Row).

Afternoon: Choose the Shedd Aquarium (shimmering Caribbean Reef and playful belugas) or Adler Planetarium (stellar shows and the best downtown panorama from the peninsula). Walk Northerly Island if the weather is kind. Late lunch at Eleven City Diner (hearty Reubens, matzo ball soup) or Cafecito (Cuban sandwiches and cafecito pick‑me‑ups).

Evening: Pizza night at Pequod’s (caramelized crust edges—many locals’ favorite). Then catch live music: the Green Mill (Uptown) for jazz under art‑deco neon, or Kingston Mines (Lincoln Park) for rollicking blues across two stages.

Day 4: Lincoln Park Greenspaces, Wrigleyville, and Comedy

Morning: Breakfast in Lincoln Park: Wildberry Pancakes (berry bliss), Ann Sather (legendary cinnamon rolls), or Elaine’s Coffee Call (quiet, vintage feel). Wander the free Lincoln Park Zoo and Lincoln Park Conservatory; stroll the Alfred Caldwell Lily Pool for a serene, Wright‑inspired landscape. If it’s beach weather, detour to North Avenue Beach or walk a stretch of the Lakefront Trail.

Afternoon: Head to Wrigleyville for a Wrigley Field tour (behind‑the‑scenes of the Friendly Confines) or browse boutiques in Southport Corridor. Lunch ideas: Portillo’s for a proper Chicago dog “dragged through the garden,” Al’s for juicy Italian beef dipped in jus, or Crisp for Korean‑style wings.

Evening: Laugh with the pros at The Second City (Old Town)—birthplace of countless comedy greats. Dine nearby: Cafe Ba‑Ba‑Reeba! (tapas and sangria), Orso’s (classic red‑sauce Italian), or Topo Gigio’s cozy patio. For craft cocktails, stop at The Violet Hour (speakeasy rules, candlelit booths) or Forbidden Root (botanical brews) in West Town.

Day 5: Hyde Park, Robie House, and Pilsen Murals

Morning: Explore Hyde Park. Breakfast at Valois (“see your food” cafeteria—Obama favorite) or Plein Air Cafe for excellent pastries and espresso. Visit the Museum of Science and Industry (coal mine, storms, and science fun), then tour Frank Lloyd Wright’s Robie House to see Prairie School design in situ. Wander the Gothic quad of the University of Chicago.

Afternoon: Head to Pilsen for color-splashed murals and the National Museum of Mexican Art (free, superb). Lunch at Carnitas Uruapan (weekend lines for crispy pork shoulder), 5 Rabanitos (fresh, produce‑driven plates), or Birrieria Zaragoza (if you’re up for a short ride for goat birria perfection).

Evening: Chinatown feast: MingHin Cuisine (dim sum hits all day), Lao Sze Chuan (fiery mapo tofu and dry chili chicken), or QXY Dumplings (hand‑pulled noodles). Dessert at Joy Yee (heaping shaved ice, bubble teas). If in season, the river water taxi between Chinatown and the Loop adds a scenic ride.

Day 6: Tastes of the Loop and River North, Navy Pier, and Fulton Market

Morning: Keep breakfast light (Firecakes Donuts or Do‑Rite’s buttermilk old fashioneds)—you’ve got a tasting tour coming up.

Afternoon: Join the Chicago Favorites Ultimate Food and Walking Tour to sample Chicago‑style pizza, hot dogs, brownies, and local sips while learning architecture and Prohibition lore between bites. It’s a flavorful primer on downtown’s icons and hidden corners.

Afterward, stroll Navy Pier for lake views and the Centennial Wheel, or unwind at Ohio Street Beach. Coffee pick‑me‑up at Foxtrot or Limitless.

Evening: Progressive dinner in Fulton Market/West Loop. Try Time Out Market for a curated cross‑section of local favorites under one roof, or book a table: Avec (Mediterranean), Publican (nose‑to‑tail and oysters), or Smyth (for a celebratory Michelin‑starred splurge). Cocktails at Lazy Bird (live jazz some nights) or The Aviary (culinary‑driven concoctions; reservations recommended).

Day 7: Sky‑High Morning, Last Bites, Departure

Morning: Start early at Lou Mitchell’s (a Route 66 legend—honey‑drizzled donut holes and skillet eggs) before riding up to the Skydeck – Willis Tower. Step onto The Ledge—glass boxes 1,353 feet over Wacker Drive—for a final, unforgettable city view. Early time slots help beat the lines.

Grab a fast lunch before you go—XOCO (wood‑roasted tortas, churros), Beatrix (healthy bowls and excellent cookies), or Pastoral (gourmet sandwiches to‑go). Pick up last‑minute souvenirs on the Magnificent Mile.

Afternoon: Head to the airport. From the Loop, budget ~45 minutes to ORD (Blue Line) or ~25 minutes to MDW (Orange Line). If driving or hailing a rideshare during rush hour, allow an extra 30–45 minutes.

Optional add‑ins if you have gaps or want to swap: Garfield Park Conservatory (free, lush sanctuary); Andersonville’s indie shops and Swedish heritage; Wicker Park’s boutiques and The 606 trail; 360 CHICAGO for different views over Lake Michigan (tilt attraction); the Chicago Cultural Center’s Tiffany dome; Fly a kite or picnic on Montrose Beach.

Viator experiences featured in this itinerary:

• Chicago River 90-Minute Architecture Tour
• Field Museum of Natural History Admission Tickets
• Chicago Favorites Ultimate Food and Walking Tour
• Skydeck – Willis Tower Admission

Booking reminders: Reserve popular restaurants 2–4 weeks ahead (longer for Fridays/Saturdays), and observation decks around sunset. For flexible pricing on flights, compare dates on Trip.com and Kiwi.com, then lock in accommodations via Hotels.com Chicago or VRBO Chicago.

In a week, you’ll have seen Chicago from the river, the lake, and the sky—and tasted it from doughy edges to refined tasting menus. This itinerary balances blockbuster sights with neighborhood texture, so your memories aren’t just of buildings, but of the stories—and flavors—inside them.