The United States is built for big-city adventures, and few pair better than New York City and Chicago. One is a 24/7 collage of neighborhoods, Broadway lights, and global cuisine; the other, a lakeside masterpiece of steel and glass where world-changing architecture meets Midwestern warmth. In one week, you’ll walk famed avenues, savor bagels and deep-dish, and glide past skyline legends on the river.

New York’s layered history—from Dutch outpost to cultural capital—meets Chicago’s rebirth after the 1871 Fire, when architects forged the modern skyscraper. Museums are world-class, parks are proudly public, and neighborhoods offer distinct flavors: dim sum in Manhattan’s Chinatown, tacos in Pilsen, jazz in Greenwich Village and blues in Lincoln Park.

Practical notes: Expect walkable days with easy subway and “L” train connections. Book timed tickets for viewpoints and popular museums. For flights, compare fares on Trip.com and Kiwi.com; subways and rideshares cover most city moves. Dress in layers, carry a refillable water bottle, and bring comfy shoes—the sidewalks are the real attraction.

New York City

Welcome to the city where every block tells a story. Start with Midtown’s icons, wander leafy Greenwich Village lanes, and cross the Brooklyn Bridge for postcard views. Eat your way through bagel shops, slice joints, and sleek bistros—food is half the fun.

• Top sights: Central Park, The Met, 9/11 Memorial, Brooklyn Bridge, Times Square, Grand Central, High Line, West Village.
• Don’t miss: A harbor or skyline cruise at sunset, a neighborhood food crawl, and one night of live music or Broadway.
• Neighborhood flavor: Dumplings on Mott Street, Neapolitan pies in the Village, and speakeasy cocktails in Lower Manhattan.

Where to stay: For more space or family trips, browse apartments on VRBO New York City. For hotels across Midtown, SoHo, and the Village, compare deals on Hotels.com New York City.

Getting in: JFK to Midtown is ~60–75 minutes via AirTrain + subway; a yellow cab runs flat-fare to Manhattan. From Newark (EWR), NJ Transit to Penn Station takes ~35–45 minutes. Find flights on Trip.com or Kiwi.com; typical domestic fares range ~$120–$350 roundtrip depending on season.

Day 1: Arrival, Midtown Icons, and K-Town Supper

Afternoon: Arrive and check in. Stretch your legs through Bryant Park and the New York Public Library’s marble halls, then pop into Grand Central to admire the celestial ceiling and grab an espresso at Culture Espresso or Joe Coffee inside the station.

Evening: Walk Fifth Avenue to Rockefeller Center for street-level views of the plaza and art deco reliefs. Dinner in nearby Koreatown: Jongro BBQ for charcoal-grilled short rib, Her Name Is Han for cozy home-style stews, or Take 31 for small plates and soju. Nightcap at The Rum House off Times Square—live piano, old New York vibe.

Day 2: NYC in One Day + Skyline at Sunset

Spend the day on the New York in One Day Guided Sightseeing Tour—a guide hops off with you at key stops, stitching neighborhoods and landmarks into a vivid story. Expect Times Square, Central Park, Wall Street, and more in about 6 hours, with breaks for photos and snacks.

Post-tour dinner: Hell’s Kitchen favorites like Pure Thai Cookhouse (boat noodles, wok char) or Tulcingo Del Valle (Puebla-style mole). Time your entry for sunset at SUMMIT One Vanderbilt, where mirrored rooms and 360-degree views turn golden hour into an art show above the Chrysler Building.

Day 3: Brooklyn Bridge, DUMBO, and a Night on the Water

Morning: Cross the Brooklyn Bridge at sunrise to beat the crowds. Coffee at Devoción in DUMBO (Colombian beans roasted on-site) and photos from Washington Street with the Manhattan Bridge perfectly framed. Browse Empire Stores and stroll Brooklyn Bridge Park’s piers.

Afternoon: Back in Manhattan, explore SoHo and Nolita boutiques. Lunch ideas: Sadelle’s for smoked fish platters, Rubirosa for a perfect thin-crust vodka pie, or Los Tacos No. 1 for griddled adobada. Detour to the 9/11 Memorial for reflection beneath the oaks.

Evening: Sail past Lady Liberty on the Starship 90-Minute NYC Cruise; multiple departures include sunset and city-lights runs for dramatic photos of bridges and the skyline.

Late bite in the West Village: Via Carota (Tuscan small plates), L’Artusi (modern Italian, exceptional pastas), or Buvette (Parisian-style comfort). If you’ve got energy, jazz at Village Vanguard or Smalls.

Day 4: The Met, Central Park, and Broadway Night

Morning: Bagels at Ess-a-Bagel (get the everything with scallion cream cheese and lox) or breakfast at Daily Provisions (maple crullers, bacon-egg-cheese on a roll). Head to The Met—start with the Temple of Dendur, then choose a wing (European masters or Arms and Armor are crowd-pleasers).

Afternoon: Wander Central Park: Bethesda Terrace, Bow Bridge, and the Ramble. Rent a rowboat at Loeb Boathouse in season or explore the Conservatory Garden uptown. Late lunch at The Modern Bar Room near MoMA (share plates, slick service) or Luke’s Lobster for a quick roll.

Evening: Catch a Broadway or Off-Broadway show—buy official same-day tickets at TKTS or theater box offices. Pre- or post-show, dine at Joe Allen (industry haunt), Gallaghers for classic steaks, or Don Antonio for Neapolitan-style pies with a fried montanara twist.

Chicago

Chicago rises on Lake Michigan like a city drawn with a ruler, then softened by beaches, parks, and the Riverwalk. Here, modern architecture was born, blues music hums late, and chefs play with Midwest bounty from farmers and Great Lakes fisheries.

• Top sights: Millennium Park, The Art Institute of Chicago, Riverwalk, Willis Tower, Wrigley Field (in season), Museum Campus.
• Must-do: An architecture river cruise—see why the skyline is a living museum of form and function.
• Eat & drink: Deep-dish and tavern-style pizza, Italian beef, innovative West Loop kitchens, third-wave coffee, and speakeasy cocktails.

Where to stay: Search apartments and condos on VRBO Chicago or compare hotel neighborhoods (Loop, River North, West Loop, Gold Coast) on Hotels.com Chicago.

Getting there from NYC: Morning flights from JFK/LGA/EWR to ORD/MDW take ~2.5 hours. Typical one-way fares range ~$80–$250; compare on Trip.com and Kiwi.com. From O’Hare, the Blue Line reaches the Loop in ~45 minutes; from Midway, Orange Line does it in ~25 minutes.

Day 5: Fly to Chicago, Millennium Park, and Deep-Dish

Morning: Depart New York on an early flight (~2.5 hours). Grab a light breakfast at the airport (oat milk latte + egg sandwich keeps you going). On arrival, take CTA into the Loop and drop bags.

Afternoon: Walk Millennium Park: take the photo at “Cloud Gate” (The Bean) and sit by Crown Fountain’s playful faces. Lunch at Revival Food Hall (local vendors under one roof—try Smoque for BBQ or Antique Taco), then an hour at The Art Institute for American Gothic and the Thorne Miniature Rooms.

Evening: Deep-dish dinner: Lou Malnati’s (buttery crust, bright tomato sauce), Pequod’s in Lincoln Park (caramelized cheese crust devotees’ favorite), or Giordano’s for stuffed style. Nightcap at Cindy’s Rooftop for sweeping park and lake views.

Day 6: Neighborhood Coffee, Architecture Cruise, and Blues

Morning: Explore Wicker Park and Bucktown boutiques. Coffee at Intelligentsia (a Chicago original) or Ipsento (try a honey latte). Quick bites: Stan’s Donuts or Mindy’s Bakery for an indulgent start.

Afternoon: Join the classic Chicago Architecture River Cruise to learn how Burnham, Wright’s contemporaries, and today’s starchitects reshaped a city—watch for the Tribune Tower, Marina City “corncobs,” and the glittering river canyon.

Evening: Dinner in the West Loop: Girl & the Goat (global small plates), Monteverde (handmade pasta), or The Publican (Midwest meats and shellfish). Cap the night with live blues at Kingston Mines (two stages, late sets) or Buddy Guy’s Legends near the Loop.

Day 7: Brunch, Riverwalk Stroll, and Departure

Morning: Brunch at Beatrix (healthy-ish hits, bakery case) or The Publican’s Sunday spread if timing aligns. Stroll the Chicago Riverwalk—watch kayakers slip beneath bridges and pop into Office Hours for an espresso or a final gelato.

Afternoon: Last-minute shopping along the Magnificent Mile or a quick selfie at the Wrigley Building. Head to the airport: Blue Line to O’Hare (~45 minutes) or Orange Line to Midway (~25 minutes). Compare return flight options on Trip.com or Kiwi.com.

Where to Sleep Each Night

• Nights 1–4 (New York City): Base in Midtown for easy transit to sights, or the Village for nightlife and dining. Browse VRBO and Hotels.com by neighborhood.
• Nights 5–6 (Chicago): River North and the Loop are walkable to the Riverwalk and Millennium Park; West Loop is foodie central. Compare stays on VRBO and Hotels.com.

Getting Between Cities

NYC → Chicago (Day 5, morning): 2.5-hour nonstop flights are frequent on major carriers. Typical fare ranges ~$80–$250 one-way. Check schedules and prices on Trip.com Flights and Kiwi.com Flights. Aim to depart by 8–9 am to maximize your Chicago afternoon.

Optional add-ons if you have extra time: A Yankees, Mets, Cubs, or White Sox game; the High Line and Hudson Yards in NYC; or a detour to the Museum Campus in Chicago for the Field Museum and Shedd Aquarium.

Viator activities featured in this itinerary:

• New York in One Day Guided Sightseeing Tour
• SUMMIT One Vanderbilt Experience Ticket
• Starship 90-Minute NYC Cruise
• Chicago Architecture River Cruise

In one week, you’ll trace the story of American cities—from Broadway brio and bagel shops to riverfront reinvention and deep-dish comfort. Expect full days, big views, and the kind of meals you’ll reminisce about long after your flight home.