Comparison · United States
Chicago vs New York: Which Should You Pick First?
Lakefront Chicago or museum-and-skyline New York City? Who each suits, airport transfers, days, budget, monthly weather and sights, from our two guides.
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The short answer
Chicago is a big American city on Lake Michigan, known for historic architecture, its riverside walkway and free parks and lakefront. You can tour Millennium Park, the Art Institute of Chicago and the lakefront museums, and try local classics such as deep-dish pizza and the Chicago-style hot dog.
New York City brings museums, Broadway, the skyline and food from around the world together in one city. Manhattan's grid makes navigation easy, and the 24-hour subway and walking cover most of it. The guide also warns that hotels and prices run high, so budget planning matters.
Best for: Chicago suits travelers who want architecture, lakefront walks and free parks and sights over 3 to 4 nights. New York City suits travelers who want museums, shows and the skyline on foot over 4 to 6 nights.
From the airport to the city
At Chicago's O'Hare International Airport (ORD), CTA Blue Line trains run 24 hours a day, and every train goes through downtown. From Terminals 1, 2 and 3, follow the 'Trains to City' signs through the basement tunnels; from Terminal 5, where international flights arrive, take the airport train (ATS) to Terminal 2 or 3 first. Take taxis only from the stands at the lower-level curb outside baggage claim, and do not accept rides from drivers outside the stand or on the departure level.
New York City has several airports. From JFK, the AirTrain to Jamaica or Howard Beach and then the subway into Manhattan is the cheapest option. From Newark (EWR), take the AirTrain and NJ Transit to Penn Station; from LaGuardia (LGA), the free Q70 bus runs to Jackson Heights, where you transfer to the subway.
- Chicago CTA Blue Line: about 40-45 min to downtown, USD 5 (no extra charge with a 1-, 3- or 7-day pass)
- Chicago taxi: about 25-90 min to downtown depending on traffic, about USD 50 on average plus tip
- Chicago Metra commuter train (North Central Service): to Union Station downtown, weekdays only (check the official timetable and fares)
- New York City, JFK AirTrain + subway: about 60-75 min, about USD 11-12
- New York City, JFK yellow cab: about 45-75 min depending on traffic, about USD 70 flat plus tolls and tip
- New York City, EWR AirTrain + NJ Transit: about 30-40 min, about USD 16-18
- New York City, LGA Q70 bus + subway: about 45-60 min, about USD 3 (subway fare)
How many days, and how much?
The guides suggest 3 to 4 nights for Chicago and 4 to 6 nights for New York City.
Budgets are hard to compare like for like. For New York City, daily totals come in low, mid-range and high levels. For Chicago, plan around transport costs and free sights; hotel and food costs vary a lot by date, so check booking sites. That means the two cities' daily budgets cannot be compared side by side in numbers.
On the New York City subway, after 12 paid rides within 7 days on the same card (OMNY), the rest of that week is free. Listed prices in New York City exclude sales tax (about 8.875%), so expect a higher total at checkout.
- New York City daily budget: low about USD 120-150, mid about USD 300-400, high about USD 700+
- Chicago transport: USD 2.50 per 'L' ride, USD 2.25 per bus ride, unlimited passes USD 5 (1 day), USD 15 (3 days), USD 20 (7 days)
- Chicago free sights: Millennium Park, the Chicago Cultural Center, Lincoln Park Zoo and the beaches
- New York City food: pizza slice about USD 4-6, bagel about USD 5-15, food hall meal about USD 15-25
- Tipping: in Chicago about 20% of the pre-tax bill for taxis, restaurants and bars; in New York City usually 15-20% of the pre-tax bill at restaurants
Weather month by month
The guides' best times are June to September in Chicago (average highs of 24-29°C, warm enough for lakefront walks and boat tours) and April to June and September to November in New York City (the most pleasant walking weather). The overlap, June and September, works well for both.
The figures below are NOAA National Centers for Environmental Information (NCEI), U.S. Climate Normals (1991–2020): Chicago O'Hare International Airport station for Chicago and New York Central Park station for New York City. Each line shows the same month's average high/low and precipitation.
The Chicago guide says April to August gets more rain, at 94-114 mm a month, and December to February is very cold, with average highs of 0-3°C and lows of -7 to -4°C. In New York City, July and August are hot and humid, and January to February can be bitterly cold. New York City's holiday season (Thanksgiving to New Year) is magical, but hotel prices spike.
- January: Chicago 0/-7°C, 51 mm; New York City 4/-2°C, 93 mm
- April: Chicago 15/5°C, 95 mm; New York City 17/8°C, 104 mm
- June: Chicago 27/16°C, 104 mm; New York City 27/18°C, 115 mm
- September: Chicago 24/14°C, 81 mm; New York City 25/17°C, 110 mm
- October: Chicago 17/7°C, 87 mm; New York City 18/11°C, 111 mm
What you do there
In Chicago, much of your time centers on the Loop, the official downtown. Millennium Park, a free park with Cloud Gate (nicknamed 'The Bean') and Crown Fountain, the Art Institute of Chicago, the country's second-largest art museum, the Chicago Cultural Center with its two stained-glass domes (free, daily 10 a.m.-5 p.m.) and the Riverwalk on the south bank of the Chicago River are all close together. Many architecture boat tours leave from the Riverwalk, and most run from spring to autumn.
On the lakefront are the Museum Campus with the Field Museum, Shedd Aquarium and Adler Planetarium, Navy Pier with its Ferris wheel, and the free Lincoln Park Zoo and Conservatory. Repairs on the Lakefront Trail began on 14 September 2026 and will continue for several months, so check for closures. Beach swimming is allowed only from the Friday before Memorial Day to Labor Day, 11 a.m.-7 p.m., when lifeguards are on duty.
New York City is a city to explore on foot. Classic stops include Central Park, the Metropolitan Museum of Art (closed Wednesdays), the Statue of Liberty by official ferry from Battery Park, the Brooklyn Bridge, the High Line, the 9/11 Memorial, and Times Square and Broadway. If you choose one observation deck, go at sunset; the free Staten Island Ferry from the southern tip of Manhattan also gives views of the Statue of Liberty and the skyline.
- Chicago food: the Chicago-style hot dog (no ketchup, by tradition), deep-dish pizza, Italian beef, the jibarito, and tacos in Pilsen and Little Village
- New York City food: pizza slices, bagels, pastrami sandwiches, food halls, dim sum in Chinatown and Korean food in Koreatown (32nd Street)
- First-timer base: the Loop in Chicago, Midtown (around Times Square) in New York City
- Dining neighborhoods: West Loop in Chicago, Chelsea and Greenwich Village in New York City
- Nature and a calmer feel: Lincoln Park (park, zoo, lakefront) in Chicago, the Upper West Side next to Central Park in New York City
How to choose, and what to check before you go
Choose Chicago for architecture, the lakefront and free parks and sights; choose New York City for museums, shows and the skyline on foot. Both guides include a 4-day sample itinerary, so if you visit both cities on one trip, use each itinerary to split your days.
US entry requirements (visa, travel authorization, etc.) can change. Always check the U.S. government's official information before you travel.
- Chicago: take airport taxis only from the stand; fares are metered
- Chicago: pack a warm coat, gloves and a hat for December to February; local temperatures are shown in Fahrenheit (°F)
- New York City: costumed characters and people handing out CDs in Times Square will ask for money; politely decline
- New York City: late at night, ride in subway cars with other people and keep your phone and bag close
Plan your Chicago trip
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Plan your New York City trip
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FAQ
For a first US trip, should I choose Chicago or New York City?
Chicago suits you if you want architecture, the lakefront and free parks over 3 to 4 nights; New York City suits you if you want museums, shows and the skyline on foot over 4 to 6 nights.
Which one costs more?
The two guides present budgets differently, so their numbers cannot be compared side by side. The New York City guide puts a mid-range day at about USD 300-400; the Chicago guide lists transport costs (such as a USD 5 1-day pass) and free sights, and says to check booking sites for hotels and food.
When is a good time to visit both cities?
June and September, where the guides' best times overlap. Chicago is very cold from December to February, and in New York City July and August are hot and humid while January to February can be bitterly cold.
Can I get from the airport to the city by public transport?
Yes. In Chicago, the CTA Blue Line runs 24 hours from O'Hare International Airport and takes about 40-45 minutes to downtown for USD 5. In New York City, use the AirTrain + subway from JFK (about USD 11-12) or the free Q70 bus + subway from LaGuardia (about USD 3).
Related reading
ⓘ Photo credits
- Buckingham Fountain, Grant Park · Ken Lund / CC BY-SA 2.0
- Brooklyn Bridge · Suiseiseki / CC BY-SA 3.0
- Downtown Los Angeles skyline from Griffith Observatory · Daniel L. Lu (user:dllu) / CC BY-SA 4.0