USA Multi-City Itinerary: New York, Chicago, Los Angeles
A coast-to-coast multi-city itinerary combining New York, Chicago, and Los Angeles — three of America's most distinct cities, with practical routing, timing, and booking advice.
USA Multi-City Itinerary: New York, Chicago, Los Angeles
New York, Chicago, and Los Angeles form a genuinely coast-to-coast introduction to the United States — three cities with almost nothing in common beyond the flag flying over them. New York’s density and energy, Chicago’s architecture and Midwest civility, LA’s sprawl and climate together give a far more complete picture of the country than any single city could on its own.
This guide covers how to combine the three, how to move between them, how long to spend in each, and the practical details — particularly around US immigration and domestic connections — that are worth understanding before you book.
Why This Combination Works
Geographically, the three cities form a rough line across the continent — New York on the East Coast, Chicago in the Midwest, Los Angeles on the West Coast — meaning a route that moves in one direction avoids backtracking entirely.
Each city also represents a genuinely different American experience. New York is walkable, dense, and relentless. Chicago combines big-city energy with a more manageable scale and some of the best 20th-century architecture in the world. Los Angeles trades density for space, car culture, and a climate that barely resembles the other two. Visiting all three in one trip gives a far more accurate sense of the country’s range than concentrating on one region.
Suggested Route and Timing
London → New York → Chicago → Los Angeles → London
This order moves from east to west, finishing on the Pacific coast — a logical routing that also positions you well for a return flight home or an onward extension to Asia or the South Pacific if you have more time.
Total trip length: 12–16 days
- New York: 4–5 days
- Chicago: 3 days
- Los Angeles: 5–7 days
Entering the USA: What UK Travellers Need to Know
ESTA Requirement
UK passport holders travelling to the US for tourism under the Visa Waiver Program need an approved ESTA (Electronic System for Travel Authorization) before departure. Apply online at least 72 hours before travel, though doing so several weeks in advance is strongly recommended in case of any issues. The ESTA typically remains valid for two years or until your passport expires, whichever comes first.
Immigration on Arrival
You’ll clear US Customs and Border Protection at your first point of entry into the country — in this itinerary, that’s New York. This is worth planning around, since it can take anywhere from 30 minutes to over 2 hours depending on the time of day and how many international flights have landed simultaneously. Build in a generous buffer if you have any onward connection on the same day you arrive (not applicable in this itinerary, since New York is the first stop, but relevant if your route differs).
Domestic Connections Within the US
Because immigration is cleared at the first entry point, all subsequent domestic flights within this itinerary (New York → Chicago, Chicago → Los Angeles) are treated as standard domestic connections — no further immigration formalities, just standard TSA security screening.
New York: 4–5 Days
Getting There
London → New York (JFK or Newark) is roughly 7–8 hours direct, served by numerous carriers including British Airways, Virgin Atlantic, American Airlines, Delta, and United.
What to Prioritise
Manhattan on foot — the most rewarding way to experience New York is simply walking between neighbourhoods: the West Village, SoHo, the Lower East Side, and Midtown each have a distinct character within a relatively small area.
Central Park and the Museum Mile — the Metropolitan Museum of Art alone justifies a half-day; the park itself is worth an unhurried few hours regardless of season.
The High Line and Chelsea Market — an elevated former rail line turned park, connecting neatly to one of the city’s best food halls.
A Broadway show — genuinely worth the cost even for those who don’t consider themselves theatre-goers; TKTS booths in Times Square and Union Square offer same-day discounted tickets for many shows.
The Brooklyn Bridge and DUMBO — walk across at golden hour for one of the city’s best skyline views, then explore Brooklyn’s waterfront neighbourhoods.
Practical Notes
- The subway is the most efficient way to get around and runs 24 hours; a contactless card or phone payment works directly at the turnstiles.
- New York is expensive by nearly any measure — budget accordingly for accommodation in particular.
- Spring (April–June) and autumn (September–November) offer the most comfortable weather; summer can be intensely hot and humid.
Chicago: 3 Days
Getting There
New York → Chicago is approximately 2h30 direct, with frequent services throughout the day on American, United, and Delta.
What to Prioritise
Architecture river cruise — widely considered one of the best city tours in America, covering Chicago’s landmark buildings from the water with expert commentary on the city’s architectural history.
Millennium Park and Cloud Gate (“The Bean”) — the city’s most photographed modern landmark, alongside a genuinely excellent public park.
The Art Institute of Chicago — one of the finest art museums in the US, with an outstanding Impressionist collection.
Deep-dish pizza — a genuinely worthwhile culinary experience despite the tourist reputation; Lou Malnati’s and Giordano’s are the most famous names, though many locals have their own preferred spot.
Willis Tower Skydeck or 360 Chicago (Hancock Tower) — either offers spectacular views; 360 Chicago is generally less crowded and slightly cheaper.
Practical Notes
- Chicago’s grid layout makes it one of the more straightforward American cities to navigate, whether on foot, by the ‘L’ train system, or by taxi/rideshare.
- Lake Michigan’s presence gives Chicago a genuinely coastal feel in summer, with excellent lakefront paths and beaches.
- Winters are notoriously cold and windy — if visiting between November and March, pack accordingly.
Los Angeles: 5–7 Days
Getting There
Chicago → Los Angeles is approximately 4h15 direct, served by American, United, Delta, and several others.
What to Prioritise
Santa Monica and Venice Beach — the classic LA beach experience, with Venice’s boardwalk offering some of the city’s most distinctive people-watching.
Griffith Observatory — free admission, spectacular views over the city and the Hollywood Sign, particularly impressive at sunset.
Downtown LA and the Arts District — a genuinely different side of the city from the beach and Hollywood stereotypes, with excellent food and a growing gallery scene.
A day trip along the coast — renting a car for a day to drive part of the Pacific Coast Highway, even just as far as Malibu, is one of the best ways to experience Southern California’s coastline.
Griffith Park and the Hollywood Sign hike — for those wanting a more active day, several trails lead close to the iconic sign with excellent city views along the way.
Practical Notes
- Los Angeles is genuinely difficult to navigate without a car — public transport exists but coverage and frequency are inconsistent compared to New York or Chicago. Renting a car for at least part of your stay is worth considering.
- Traffic is a serious consideration when planning your days — journeys that look short on a map can take considerably longer at peak times.
- The climate is consistently mild and dry for most of the year, making LA a comfortable destination regardless of when you visit, though June can bring overcast mornings (“June gloom”) along the coast.
Sample Day-by-Day Itinerary
Days 1–5: New York
- Day 1: Arrive, clear immigration, settle in, evening walk in Midtown
- Day 2: Central Park, Metropolitan Museum of Art
- Day 3: SoHo, the High Line, Chelsea Market
- Day 4: Brooklyn Bridge, DUMBO, Brooklyn waterfront
- Day 5: Free morning, afternoon flight to Chicago
Days 6–8: Chicago
- Day 6: Arrive, evening in Millennium Park
- Day 7: Architecture river cruise, Art Institute
- Day 8: Willis Tower or 360 Chicago, deep-dish dinner, afternoon flight to LA
Days 9–14: Los Angeles
- Day 9: Arrive, settle in, evening in Santa Monica
- Day 10: Venice Beach, Abbot Kinney Boulevard
- Day 11: Griffith Observatory, Hollywood
- Day 12: Downtown LA and the Arts District
- Day 13: Coastal day trip (Malibu or further up the PCH)
- Day 14: Free day, departure preparations
Day 15: Fly home
Budget Considerations
All three cities are relatively expensive by international standards, though costs vary:
New York: The most expensive of the three for accommodation, comparable to major European capitals. Food ranges enormously — excellent budget options exist alongside very high-end dining.
Chicago: Generally more affordable than New York for both accommodation and dining, while still offering a genuine big-city experience.
Los Angeles: Accommodation costs vary enormously by neighbourhood — Santa Monica and Beverly Hills carry a significant premium over more central or eastern parts of the city. A rental car adds a meaningful cost that should be factored into the overall budget.
Extending the Trip
If you have additional time, a few natural extensions fit well into this route:
San Francisco — easily added as a stop between Chicago and Los Angeles, or as an extension after LA, roughly 1h20 by air from either city.
Las Vegas — a short flight or drive from Los Angeles (around 1 hour by air, 4 hours by road), suitable as a 2–3 day addition for those interested in the contrast it offers.
Washington DC — if flying via the East Coast, DC is a straightforward addition either before or after New York, with excellent free museums and a completely different civic atmosphere.
Final Thoughts
New York, Chicago, and Los Angeles together offer one of the most complete introductions to the United States available in a single trip — three genuinely different cities, connected by short, frequent domestic flights, with no backtracking required if you route the trip in a logical east-to-west direction.
Twelve to sixteen days gives each city fair time without feeling rushed, though the itinerary compresses reasonably well to 10 days if needed, or extends comfortably with additions like San Francisco or Las Vegas for those with more time.
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