Two American icons. One ambitious 14-day itinerary. You’ll trace Chicago’s shimmering river canyons and storied neighborhoods before swapping Midwestern grit for Southern California glam—studios, sunsets, and the hum of the Pacific. Along the way: great coffee, can’t-miss museums, and restaurants locals actually love.

Chicago rose from the Great Fire of 1871 to become an open-air museum of modern architecture. Its lakefront parks, blues bars, and legendary food scene make it a joy in any season. Los Angeles, meanwhile, is a quilt of villages—Hollywood history in the hills, beach culture by day, and a global dining scene after dark.

Practical notes: In Chicago, the ‘L’ drops you right downtown; in LA, a rental car or rideshares save time across sprawling neighborhoods. Book timed tickets for popular observation decks and studio tours. Pack for layers—breezy lakefronts in Chicago, cool desert evenings in LA—and always reserve dinner hotspots ahead.

Chicago

Welcome to the birthplace of the skyscraper, where Frank Lloyd Wright experimented in brick and steel and 20th-century titans redrew the skyline. Between the Riverwalk, Millennium Park, and the lakefront trail, it’s easy to pair big sights with relaxed strolls and a steady stream of great eats.

Getting here and getting around: Fly into O’Hare or Midway. Compare fares on Trip.com or Kiwi.com. The CTA Blue Line from O’Hare takes about 45 minutes to the Loop (about $5 from the airport); the Orange Line from Midway is roughly 25 minutes. Rideshares to downtown run ~30–60 minutes depending on traffic.

Days 1–3: The Loop, Riverwalk, and Skyline Icons

• Start on the water. Chicago’s story is best told from a boat, where every bend reveals a new chapter in urban design.

Chicago Architecture Center River Cruise aboard First Lady

• Millennium Park and the Art Institute. Gaze into “Cloud Gate,” then cross to the Art Institute for Grant Wood, Impressionists, and modern masters. Stroll the Nichols Bridgeway to Maggie Daley Park for skyline photos.
• Elevated views. Step onto the glass ledges on the 103rd floor.

Skydeck - Willis Tower Admission

• Eat like a local. Breakfast at Wildberry Pancakes & Cafe (signature berry bliss), or Lou Mitchell’s (since 1923) for eggs and fresh-baked doughnut holes. Coffee at Intelligentsia (Monadnock) or Sawada Coffee (West Loop, military latte).
• Deep dish and more. Try Lou Malnati’s (buttery crust) or Pequod’s (caramelized edge). For a lighter bite, Portillo’s for a Chicago dog “dragged through the garden.”
• Evening options. Blues at Kingston Mines, cocktails at Three Dots and a Dash, or a twilight walk on the Riverwalk.

Days 4–5: Museum Campus, Chinatown, and Hyde Park

• Museum Campus trifecta. Pair the Field Museum’s SUE the T. rex with Shedd Aquarium’s Caribbean Reef and lakefront views from the Adler peninsula.
• Chinatown dumpling crawl. Mix classics and modern bakes; look for barbecue pork buns and hand-pulled noodles on Wentworth Avenue.
• Hyde Park detour. Explore the University of Chicago’s Gothic quads and the Museum of Science and Industry’s Victorian-era “Great Hall” exhibits.
• South Side eats. Virtue in Hyde Park (Southern flavors with finesse) or bridge to Pilsen for Mexican street food and vibrant murals along 18th Street.

Days 6–7: Neighborhoods—From Wicker Park to Wrigleyville

• Wicker Park & Bucktown. Start at The 606 elevated trail, browse record shops, and fuel up at Stan’s Donuts or Bang Bang Pie & Biscuits.
• West Loop’s dining district. Reserve Monteverde (handmade pastas), Girl & the Goat (global small plates), or The Publican (brasserie meats and shellfish). Metric Coffee for a midafternoon pick-me-up.
• Lincoln Park & the Lakefront. Visit the free Lincoln Park Zoo, then hire bikes along the Lakefront Trail for views back toward the skyline.
• Baseball night. Catch the Cubs at Wrigley Field or the White Sox on the South Side—ballpark snacks included.

Optional evening on the lake:

Lake Michigan Sunset Cruise in Chicago

Consider a guided tasting to sample several Windy City classics in one afternoon:

Chicago Favorites Ultimate Food and Walking Tour

Into true crime lore? Ride along with stories of Capone-era Chicago:

Chicago Crime and Mob Bus Tour

Where to stay in Chicago: Search stays on VRBO or Hotels.com. Top picks: The Peninsula Chicago (refined service steps from the Mag Mile), Freehand Chicago (stylish, budget-friendly in River North), and Embassy Suites by Hilton Chicago Downtown Magnificent Mile (roomy suites, great for families).

Chicago to Los Angeles travel: Take a morning nonstop flight (about 4–4.5 hours, often ~$120–$250 one-way; add airport time). Compare options on Trip.com and Kiwi.com. Aim to land before noon to enjoy an LA afternoon.

Los Angeles

LA is a city of neighborhoods—each with its own rhythm. One morning you’re under the Hollywood Sign; by sunset you’re watching surfers at Venice or dining in a glossy Arts District warehouse. The trick is to cluster your days by area and let the city’s story unfold.

Arrival tips: From LAX, the FlyAway bus to Union Station takes ~35–60 minutes; rideshares to Hollywood, Santa Monica, or Downtown are ~30–90 minutes depending on traffic. The Metro base fare is about $1.75 with transfers; plan extra time if using public transit across long distances.

Days 8–10: Hollywood Hills, Griffith, and Studio Magic

• First look at LA. Get oriented with a comprehensive city tour—hilltop views, iconic boulevards, and beach stops without the parking hassle.

Full-Day Iconic Sights of LA, Hollywood, Beverly Hills, Beaches and More

• Griffith Observatory hike. Walk the fire roads in Griffith Park for views of the Hollywood Sign and Downtown’s skyline, then explore the exhibits and public telescopes (plan for sunset). Coffee/brunch before or after at The Trails Cafe (rustic pies and avocado toast) or Maru Coffee in Los Feliz (single-origin pours).
• Behind the scenes in Burbank. Sit on famous sets, cruise the backlot, and see how your favorite shows come to life.

Warner Bros. Studio Tour Hollywood

• Hollywood heritage. Walk the stars on the Walk of Fame, see the TCL Chinese Theatre handprints, and peek at the Dolby Theatre. Dinner at Musso & Frank Grill (old Hollywood steaks and martinis) or L’Antica Pizzeria da Michele (Neapolitan pies in a courtyard).

Days 11–12: Santa Monica, Venice, and Malibu

• Beach day. Rent bikes on the Marvin Braude Bike Trail from Santa Monica to Venice for murals, skate parks, and Muscle Beach nostalgia. Lunch at The Albright on the Pier (seafood platters) or Gjusta in Venice (smoked fish, baked goods, patio seating).
• Museums with views. Spend an afternoon at the Getty Center (Richard Meier architecture and gardens) or the Getty Villa in Pacific Palisades for antiquities under cypress and sea breezes.
• Theme park thrills. Dedicate one day to LA’s blockbuster playground; go early and consider express access to minimize lines.

Universal Studios Hollywood General Admission Ticket, California

• Seafood and sunsets. In Malibu, book Malibu Farm (pier-front farm-to-table) or head back to Water Grill Santa Monica (raw bar, wild-caught fish). End with a golden-hour stroll on the beach.

Days 13–14: Downtown, Arts District, Echo Park, and Koreatown

• DTLA landmarks. Start at The Broad (free modern art—timed reservations recommended), peek into the Bradbury Building’s 1893 ironwork, then browse The Last Bookstore’s labyrinth. Lunch at Grand Central Market—try Eggslut (breakfast sandwiches), Tacos Tumbras a Tomas (hearty carnitas), or Sticky Rice (Thai comfort).
• Arts District afternoon. Murals, boutiques, and destination dining: Bestia (house-made pastas and wood-fired mains), Bavel (Middle Eastern flavors), or Girl & the Goat LA (bold global plates). Verve or Blue Bottle for coffee between galleries.
• Eastside reset. Pedal swan boats at Echo Park Lake with skyline views.

Swan Boat Rental in Echo Park

• Koreatown dinner. Feast at Park’s BBQ (prime cuts, banchan galore) or Kang Ho Dong Baekjeong (zippy marinades, lively vibe). Nightcap in Silver Lake at Bar Stella or a soft serve at Magpies.

Where to stay in Los Angeles: Browse neighborhoods and prices on VRBO or Hotels.com. Consider The Beverly Hills Hotel (classic hideaway on Sunset Blvd), Freehand Los Angeles (DTLA high-rise with rooftop pool), Loews Hollywood Hotel (walk to the Dolby Theatre), or Loews Santa Monica Beach Hotel (ocean views steps from the sand). For the Eastside, look at The Langham Huntington, Pasadena or DoubleTree by Hilton Hotel Los Angeles - Rosemead near the San Gabriel Valley’s stellar dining.

Coffee, breakfast, lunch, dinner—LA edition:

• Breakfast: République (croissants, shakshuka, airy atrium), Sqirl (ricotta toast, seasonal jams), Destroyer in Culver City (futurist plates, sublime pastries).
• Coffee: Alfred (melrose “but first, coffee”), Maru Coffee (precise brews), Blue Bottle or Verve for consistent single-origin espresso.
• Lunch: Bay Cities in Santa Monica (godmother sandwich), Guisados in Boyle Heights (braises on handmade tortillas), The Albright (sea-to-table on the pier).
• Dinner: Bestia or Bavel (book early), n/naka splurge (kaseki—plan months ahead), or Koreatown BBQ for interactive feasts.

Local transport tips: In LA, group sights by area to cut drive times; valet or validated parking is common. In Chicago, tap onto the ‘L’ with a reloadable Ventra card and use Divvy bikes for quick lakefront hops.

Extra LA add-ons if you have energy: The Broad’s Infinity Room (timed slots), Angels Flight funicular between Grand Central Market and Bunker Hill, or a coastal drive to El Matador State Beach for sea caves and dramatic bluffs.

Book your flights into Chicago and home from LA (or round-trip with an open-jaw) via Trip.com or Kiwi.com.

Trip wrap-up: Over two weeks, you’ll see why Chicago is the United States’ open-air architecture classroom and why Los Angeles remains the world’s favorite backlot. Expect big views, bigger flavors, and days that move from museums to beaches in one satisfying sweep.