Chicago’s story starts on the lake—an audacious city forged by industry, rebuilt after the Great Fire of 1871, and reimagined by architects who invented the modern skyline. It’s a place where blues and jazz seep from intimate clubs, where neighborhoods feel like small towns, and where a walk along the Riverwalk turns into an impromptu architecture lesson.

Beyond the icons like Millennium Park and Navy Pier, Chicago rewards curiosity. Duck into dazzling historic lobbies, sample regional staples like Italian beef and the Chicago-style hot dog, and explore neighborhoods from the West Loop’s restaurant row to the indie spirit of Wicker Park and the global flavors of Chinatown and Argyle.

Practical notes: weather swings are real—pack layers, a compact umbrella, and comfortable walking shoes. The CTA ‘L’ trains and buses cover most sights; rideshares are plentiful. As in any big city, stay aware of your surroundings at night and stick to well-traveled areas. Reservations are essential for popular restaurants, especially weekends.

Chicago

America’s architecture capital and Midwest cultural hub, Chicago marries world-class museums, Michelin-starred dining, lakefront beaches, and live music into one irresistible urban getaway. The city’s grid makes it easy to navigate, and the lake breeze keeps even hot days bearable.

• Top sights: Millennium Park & Cloud Gate, Art Institute of Chicago, Riverwalk, Museum Campus (Field Museum, Shedd Aquarium, Adler Planetarium), Willis Tower Skydeck, 360 CHICAGO, Navy Pier.
• Neighborhoods to explore: West Loop for chef-driven dining, Wicker Park for boutiques and cocktail bars, Lincoln Park for green spaces and the free zoo, Hyde Park for Gothic architecture and museums, Chinatown for incredible eats.
• What to taste: Deep-dish pizza, Italian beef, Chicago-style hot dogs (no ketchup), Garrett Mix popcorn, jibaritos, and inventive tasting menus.

Where to stay:

• The Peninsula Chicago (Five-star service, spa, and a prime Magnificent Mile location): Check rates on Hotels.com.
• Freehand Chicago (Hip design, social vibe, River North): Check rates on Hotels.com.
• Embassy Suites by Hilton Chicago Downtown Magnificent Mile (Spacious suites, family-friendly, pool): Check rates on Hotels.com.
• Browse more stays and neighborhood vacation rentals on Hotels.com Chicago or VRBO Chicago.

How to get there: Fly into O’Hare (ORD) or Midway (MDW). Compare fares and schedules on Trip.com Flights or Kiwi.com. Typical nonstop times: 1–2h from Midwest hubs, ~2–4h from coasts, 7–9h from major Latin American gateways; fares vary widely (~$150–$450 domestic roundtrip depending on season). Coming from or within Europe? Check Omio Flights.

Airport to downtown: From O’Hare, the CTA Blue Line takes ~45–55 minutes; from Midway, the Orange Line takes ~25–35 minutes. Rideshares/taxis run ~30–60 minutes depending on traffic.

Day 1: Arrival, Riverwalk, and Sunset from the Sky

Morning: Travel day. If you arrive early, grab a light bite at Goddess and the Baker (colorful cakes, solid coffee) or Do-Rite Donuts (buttermilk old fashioned) near the Loop.

Afternoon: Check in, then stretch your legs on the Chicago Riverwalk. Pause at the Vietnam Veterans Memorial, watch the bridge houses, and admire tributes to the city’s famed architects. Snack idea: a bag of Garrett Mix (cheese + caramel) for a sweet-savory Chicago classic.

Evening: Time your city intro with golden hour at the Skydeck – Willis Tower (103rd floor). Step onto The Ledge for glass-floor photos and sweeping views over Lake Michigan and the grid of lights.

Featured experience: Reserve timed admission here:

Skydeck - Willis Tower Admission

Dinner: Celebrate night one with deep-dish. Lou Malnati’s (buttery crust) is classic; Pequod’s is loved for its caramelized cheese “halo.” If you prefer lighter fare, try The Gage (upscale pub) across from Millennium Park.

Nightcap: Slip into Lazy Bird (speakeasy vibes, refined cocktails) or Billy Sunday (amaro-forward) if you’re up for one more stop.

Day 2: Millennium Park, Art, and the Architecture River Cruise

Morning: Fuel up at Wildberry Pancakes & Cafe (get the signature berry bliss pancakes) steps from Millennium Park. See Cloud Gate (“The Bean”), the Crown Fountain, and the Jay Pritzker Pavilion’s swooping steel ribbons.

Afternoon: Explore the Art Institute of Chicago—home to Seurat’s pointillist “A Sunday on La Grande Jatte,” Grant Wood’s “American Gothic,” and a stellar modern wing. Lunch nearby at Revival Food Hall for a curated mix of local vendors under one roof.

Evening: Cap the day on the water with Chicago’s signature architecture experience. Guides decode how the city pioneered the skyscraper and why styles from Art Deco to Postmodern coexist so elegantly.

Featured experience:

Chicago River 90-Minute Architecture Tour

Dinner: Head to the West Loop. Try Girl & the Goat (globally inspired small plates), Monteverde (fresh pastas), or Au Cheval (celebrated burger—expect a wait). Dessert at BomboBar (bomboloni + gelato) seals the deal.

After-hours: Classic cocktails at Moneygun, or jazz at Andy’s in River North if you want music without a late-night trek.

Day 3: Museum Campus Deep Dive

Morning: Brunch in the South Loop at Eleven City Diner (matzo ball soup, stacked sandwiches) or Yolk (banana-blueberry pancakes). Walk the lakefront to the Museum Campus with skyline views unfolding behind you.

Afternoon: Meet SUE the T. rex and explore dazzling halls at the Field Museum. Plan ~2–3 hours for highlights; more if you love natural history.

Featured experience:

Field Museum of Natural History Admission Tickets

Late afternoon: Walk to Adler Planetarium for the postcard-perfect skyline lookout. Coffee and a pastry at Spoke & Bird (Grant Park) make a nice pit stop.

Evening: Casual Chicago classics: an Italian beef “wet” with hot giardiniera at Al’s #1 Beef or Mr. Beef, then a show. Choose The Second City (improv, alumni include countless SNL stars) or the Chicago Magic Lounge (art deco room and table-side tricks).

Day 4: Lincoln Park, Beaches, and North Side Music

Morning: Start at Floriole (buttery croissants, seasonal tarts) before a stroll through the Lincoln Park Conservatory and the Alfred Caldwell Lily Pool. The free Lincoln Park Zoo is next door—small, historic, and easy to enjoy in an hour.

Afternoon: Rent bikes for the Lakefront Trail or settle into the sand at North Avenue Beach. Lunch picks: Café Ba-Ba-Reeba! (tapas and sangria) or Pequod’s if you skipped it earlier.

Evening: Head to Uptown/Andersonville. Dine at Demera (Ethiopian, perfect for sharing) or Hopleaf (Belgian beers, mussels & frites). Then take in music at the storied Green Mill (jazz, 1907 speakeasy aura) or Kingston Mines (late-night blues with rotating bands).

Day 5: Wicker Park + Bucktown, Street Art, and a Chicago Food Tour

Morning: Make a beeline to Kasama (Filipino bakery—ube and ham-and-cheese ensaymada; their Michelin-star dinner is a different experience). Explore Damen/Milwaukee/North for boutiques and vinyl shops. Coffee at Ipsento 606 before walking a stretch of the elevated 606 Trail.

Afternoon: Shift downtown for a guided tasting adventure that pairs iconic bites with city history—an easy, delicious way to cover ground and learn the stories behind the staples.

Featured experience:

Chicago Favorites Ultimate Food and Walking Tour

Evening: Back to the West Loop or stick around Wicker Park. Consider The Violet Hour (artisan cocktails, moody lounge) and dinner at Armitage Alehouse (Anglo-Indian touches, wood-paneled warmth) or Publican Quality Meats (hearty plates, stellar charcuterie). Night owls: end with live blues at Kingston Mines if you missed it yesterday.

Day 6: Hyde Park and Chinatown Farewell

Morning: Head south to Hyde Park. Breakfast at Plein Air Cafe (French-leaning pastries, excellent espresso) or Valois (old-school cafeteria—“see your food,” beloved by locals). Walk the Gothic quads of the University of Chicago and admire the exterior of Frank Lloyd Wright’s Robie House.

Afternoon: Detour to nearby Chinatown for a last great meal: dim sum at MingHin or soup dumplings at Qing Xiang Yuan, plus bubble tea for the ride. If time allows, stroll Wentworth Ave and the Nine Dragon Wall before heading to the airport for your afternoon departure.

Alternative (weather-dependent): If you skipped the river cruise earlier, consider a shorter architecture sail or a quick immersive flight experience downtown before you go.

Featured experience (optional swap if you prefer lake views by day):

Chicago Architecture River Cruise (use this if you want a shorter swap on Day 2; otherwise stick with the 90-minute tour above).

Practical Add-Ons and Tips

• Views vs. heights: If you prefer a different vantage, 360 CHICAGO offers lake-forward panoramas and the optional TILT experience. Go right at opening or for late-night views to avoid crowds.
• Transit: The CTA gets you nearly everywhere; consider a 1- or 3-day pass if you’ll ride often. Rideshares are best late at night or between far-flung neighborhoods.
• Money-savers: Clustering Museum Campus sights on one day helps. Many museums have free days for Illinois residents—non-residents should plan weekdays for thinner crowds.
• Seasonal notes: Summer brings festivals and beaches; fall colors light up parks; winter adds indoor culture, skating rinks, and cozy dining; spring is great for gardens and lighter crowds.

One more iconic pick (if you have extra time): Combine river and lake perspectives on this classic cruise:

Chicago Lake and River Architecture Tour (use this in place of the other cruise if the schedule fits better).

In six days, you’ll see the skyline from above and from the water, taste the city’s greatest hits, and meet the neighborhoods that give Chicago its character. This plan balances headliners with local haunts so your days feel full but not frantic—leaving room for serendipity along the lake.