The United States is a patchwork of cultures and skylines, and few pairings tell its story better than New York City and Chicago. New York evolved from a Dutch trading post into a global capital of art, finance, and food; Chicago rose from the Great Fire of 1871 to redefine modern architecture along its storied river. In one week, you’ll walk immigrant avenues, cruise among steel-and-glass icons, and taste the history in a bagel or a slice of deep-dish.

Expect big energy. New York’s boroughs speak more than 800 languages, while Chicago literally reversed the flow of its river to protect Lake Michigan. Museums rank among the world’s best, parks are destinations in their own right, and neighborhoods reward curious travelers who wander a block or two beyond the obvious.

Practical notes: tipping is customary (18–20% in restaurants), contactless payments are widely accepted, and both cities run reliable public transit. Winters can be icy; summers are sunny and festive. Book top sights and dining early, especially Broadway shows and popular tours. Fly into New York, then on Day 4 take a morning flight to Chicago.

New York City

New York City dazzles with contrasts: Romanesque bridges and glass spires, corner delis and Michelin stars, jazz basements and Broadway lights. Start with marquee classics, then dip into neighborhoods—Greenwich Village stoops, SoHo lofts, and waterfront strolls in DUMBO with the skyline on stage.

Top sights span Central Park’s ramble, the Met and MoMA, the High Line’s elevated gardens, and Lower Manhattan’s harbor views. Food is a throughline: bagels at dawn, dollar-slices at midnight, and everything in between.

• Where to stay (NYC): Browse apartments and vacation homes on VRBO New York City or vetted hotels on Hotels.com New York City. Aim for Midtown for transit convenience, the Village for nightlife, or the Upper West Side for a calmer base.
• How to get there: Fly into JFK, LGA, or EWR. Compare fares on Trip.com flights or Kiwi.com flights. Allow 45–75 minutes from the airport into Manhattan depending on the airport and time of day.

Day 1: Arrival, Midtown Icons, and Classic NYC Eats (Arrive afternoon)

Afternoon: Check in and stretch your legs in Bryant Park—chess boards, a carousel, and leafy views of the New York Public Library. Walk to Grand Central to admire its celestial ceiling and whispering gallery, then pass the Chrysler Building’s Art Deco crown.

Evening: Quick NYC flavors near Times Square: grab a foldable slice at Joe’s Pizza (thin, blistered crust), tacos al pastor at Los Tacos No.1 (hand-pressed tortillas), or spicy cumin lamb noodles at Xi’an Famous Foods. If you’re up for a first-night sparkle, stroll to Times Square’s neon amphitheater, best enjoyed for 15 minutes before escaping to a calmer side street dessert—Levain Bakery’s just-warm chocolate chip cookies are worth a detour.

Day 2: NYC Highlights with a Guided Overview + Broadway

Morning & Afternoon: Get your bearings with the New York in One Day Guided Sightseeing Tour. Your licensed guide leads a small group by bus and foot to essential stops—Rockefeller Center, 9/11 Memorial, Central Park photo ops—so you see a lot without logistics stress. Great for first-timers and efficient photographers.

Evening: Dinner near the Theater District: classic red-sauce pastas at Trattoria Trecolori, modern Israeli plates at Shukette Hell’s Kitchen, or Japanese comfort bowls at Tonchin. Catch a Broadway show afterward—musicals line 44th–50th Streets; buy tickets in advance and arrive 20–30 minutes early.

Day 3: Lower Manhattan, Brooklyn Views, and a Sunset Cruise

Morning: Fuel with a bagel-and-schmear at Russ & Daughters (try smoked salmon, dill, and capers) or a strong pour-over at Devoción (single-origin Colombian beans and bright, plant-filled spaces). Explore the Financial District: Trinity Church’s graveyard, the New York Stock Exchange facade, and the cobblestones of Stone Street.

Afternoon: Walk the Brooklyn Bridge into DUMBO. Photograph the Manhattan Bridge perfectly framed on Washington Street, browse Empire Stores, and grab a coal-fired pie at Juliana’s (crispy, smoky) or a burger at Time Out Market’s local vendors. Stroll Brooklyn Bridge Park for ferry views and the skyline’s grand sweep.

Evening: Take a harbor loop on the Starship 90-Minute NYC Statue of Liberty, Bridges, and Skyline Cruise for golden-hour photos and night-light magic along the East and Hudson Rivers.

Day 4: Midtown Morning, SUMMIT Views, and Fly to Chicago (Morning departure)

Morning: If you didn’t ride an observatory yet, ascend to SUMMIT One Vanderbilt—a mirrored, multi-sensory perch with wraparound Manhattan views that feels like stepping into the sky. Timed-entry tickets keep lines manageable; morning light is vivid.

Afternoon: Fly to Chicago (JFK/LGA/EWR → ORD or MDW). Nonstop flight time is ~2.5 hours; expect $80–$200 one-way if booked early. Compare options on Trip.com flights and Kiwi.com flights. From O’Hare, the Blue Line reaches the Loop in ~45–55 minutes; from Midway, the Orange Line is ~25–35 minutes.

Evening: Check in, then wander Millennium Park to meet “The Bean” (Cloud Gate) and the swooping Jay Pritzker Pavilion. Dinner: deep-dish at Lou Malnati’s (buttery crust, sausage “patty”) or caramelized-edge pan pizza at Pequod’s. Nightcap at Cindy’s Rooftop for postcard views over the park and lake.

Chicago

Chicago is the nation’s architecture classroom and a culinary playground. Frank Lloyd Wright’s Prairie School, Louis Sullivan’s ornament, and today’s glassy towers all gather along the river like a living textbook. Neighborhoods—Pilsen’s murals, Wicker Park’s indie shops, Bronzeville’s jazz lineage—reward curiosity.

Beyond architecture, you’ll find world-class museums, a waterfront unfolding for miles, and a music scene from blues to house. The lake breeze is part of the city’s identity—pack a layer even in summer.

• Where to stay (Chicago): Compare apartments on VRBO Chicago or hotels by neighborhood on Hotels.com Chicago. The Loop/River North are most central; West Loop is foodie-central; Lincoln Park is leafy and residential.
• Getting around: Load a Ventra card for CTA trains/buses; rideshares are plentiful; the Riverwalk is perfect for scenic strolls between sights.

Day 5: Art Institute, Riverwalk, and the Architecture Cruise

Morning: Breakfast at Wildberry Pancakes (near Millennium Park; get the signature berry bliss pancakes) or Do-Rite for old-fashioned donuts and coffee. Visit the Art Institute of Chicago—home to Seurat’s “A Sunday on La Grande Jatte,” Grant Wood’s “American Gothic,” and a sublime Impressionist collection.

Afternoon: Walk the Chicago Riverwalk, stopping for skyline shots under the bridges. Then board the famed Chicago Architecture River Cruise to learn how the city pioneered skyscrapers and reinvented itself after the fire—narration brings each building to life.

Evening: West Loop dinner picks on Restaurant Row: Au Cheval (legendary cheeseburger), Girl & the Goat (bold, globally-inspired small plates), or Monteverde (handmade pasta). Catch live jazz at the Green Mill—an atmospheric 1907 club where the martinis are cold and the horn sections hot.

Day 6: Lakefront, Museums, and Blues After Dark

Morning: Coffee at Intelligentsia (the local roaster that helped define third-wave coffee) and a lakefront stroll from Oak Street Beach to North Avenue Beach. For families, the Lincoln Park Zoo is free and excellent; the adjacent Conservatory is a tranquil glasshouse escape.

Afternoon: Choose your museum: Field Museum (Sue the T. rex and natural history), Shedd Aquarium (beluga whales, reef tunnels), or the Museum of Science and Industry (a captured WWII U-boat, hands-on science). Lunch nearby at Beatrix (fresh salads, hearty bowls) or the original Portillo’s for a Chicago-style hot dog “dragged through the garden.”

Evening: Explore Wicker Park’s boutiques and bars; dinner at Small Cheval (casual burger perfection) or Etta (wood-fired pizzas and pastas). Cap the night with classic Chicago blues at Kingston Mines—two stages, rotating bands, and foot-tapping until late.

Day 7: River North Brunch, Magnificent Mile, and Departure (Depart afternoon)

Morning: Brunch at The Publican (farm-driven, nose-to-tail fare; order the maple-braised bacon) or Lula Café in Logan Square (seasonal, veggie-friendly plates). Last strolls on the Magnificent Mile for architecture and shopping—Wrigley Building, Tribune Tower’s stones from global landmarks.

Afternoon: Pick up a final snack—Garrett Popcorn (sweet-salty Garrett Mix) for the plane—and head to ORD or MDW. Nonstop flights from Chicago to most U.S. hubs are frequent; compare on Trip.com flights or Kiwi.com flights.

Food & Coffee Shortlist (Save for easy reference)

• NYC breakfast/coffee: Russ & Daughters (bagels & lox), Sadelle’s (hand-rolled bagels), Devoción (Colombian coffee), Culture Espresso (cookies + cappuccinos).
• NYC lunch/dinner: Joe’s Pizza (classic slice), Juliana’s (coal-fired), Katz’s Delicatessen (pastrami on rye), Buvette (French small plates), Los Tacos No.1 (al pastor).
• Chicago breakfast/coffee: Wildberry Pancakes, Lula Café, Intelligentsia, Metric Coffee.
• Chicago lunch/dinner: Lou Malnati’s or Pequod’s (deep-dish styles), Portillo’s (Chicago dog, Italian beef), Au Cheval (burger), The Publican (hearty Midwestern plates).

Getting between cities: Plan a morning flight on Day 4. NYC → Chicago is ~2.5 hours, plus airport transfers. Budget $80–$200 one-way; book 3–6 weeks ahead for savings. Search and compare on Trip.com flights and Kiwi.com flights.

Accommodations at a glance: Browse VRBO New York City and Hotels.com New York City; then VRBO Chicago and Hotels.com Chicago for centrally located options.

In seven days, you’ll trace the American skyline from Manhattan’s spires to Chicago’s riverfront masterpieces, tasting iconic dishes and hearing the stories behind them. It’s a city-lover’s itinerary that balances big-ticket sights with neighborhood texture—enough to fall in love, and enough to leave you wanting a return trip.