New York City from Chicago, Nov 14–21: $2,088 for two, all in
The verdict
Our verdict
Worth it, if
- $244 per person, $104 below the typical fare on this route
- Pod 51 scores 8.2 from 9,513 reviews, with free cancellation
- Met or MoMA mornings, highs of 45–55°F for walking the High Line
The catch: The Frontier fare has one stop and takes 9h 30m, and Pod 51's room is a bunk pod with a shared bathroom.
Worth it if a long travel day and a bunk pod are fine for a week in New York; skip it if you need a private bathroom.
Worth it if you can live with a stop: the trip is $2,088 for two, all in. That's the Frontier fare at $488 plus 7 nights at Pod 51 for $1,600, with taxes and fees included, but resort fees, a checked bag and spending money are not in it. You leave Saturday, Nov 14, and return Saturday, Nov 21, 2026, on a Frontier flight with one stop, not a nonstop.
The total, before you go
$2,088 for two · 7 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, round trip | $488 |
| Pod 51, 7 nights, two guests, taxes in | $1,600 |
| The total, before you go | $2,088 |
| A checked bag each, round trip (not in the total) | about $240 |
$104 per person below the typical fare on this route.
Not in it: seat picks on basic fares and a checked bag (about $60 each way per bag on Frontier, $240 for two round trip); a resort fee, if the hotel has one, is collected at the desk. Prices are what we found at the time shown; the booking site’s checkout is the binding one.
The flight
$244 per person, round trip
$488 for two, taxes and fees included · Frontier · 1 stop · 9h 30m
Out Sat, Nov 14, 10:29 AM – Sat, Nov 14, 8:59 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | $244 | 1 stop | 9h 30m |
| United | $273 | nonstop | 2h 7m |
| United | $273 | nonstop | 2h 7m |
Prices checked Oct 14, 2026, 3:16 AM CDT. Prices change; the binding price is the one on the booking site.
Paid links: when you book through a link on this page, the booking site pays us a referral fee. Your price does not change. How we earn
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Why now
At $244 per person, the Frontier fare is $104 below the typical fare on this route. That's a 30% gap, and it's the lowest fare we've found on this route in 30 days. The whole week comes to $2,088 for two, all in, with Pod 51 at $1,600 for 7 nights. Resort fees, a checked bag and spending money are not in that total. We budget $190 per person a day for spending, or $2,660 for two, which brings the week to $4,748. Mid-November is coat weather, with typical highs of 45–55°F, lows near 36°F and mostly overcast skies. That works well for museum mornings, a Broadway night and long walks in between. November is also when the Macy's Thanksgiving Day Parade and the NYC Marathon happen, so check those dates against yours.
The kind of trip this is
This is a full city week: Broadway, big museums, bridges and skyline views, all on the subway. It suits a couple or two friends who like to walk all day, eat well and don't mind cold mornings. With seven nights you can take it slowly, one neighborhood a day, with time for an unhurried museum morning, instead of rushing through a long weekend.
Weather in New York City, Nov 14–21
Typical highs 45–55°F, lows near 36°F this time of year
| Day | Typical high | Typical low | Typical weather |
|---|---|---|---|
| Sat, Nov 14 | 47 °F | 35 °F | Overcast |
| Sun, Nov 15 | 49 °F | 34 °F | Overcast |
| Mon, Nov 16 | 55 °F | 38 °F | Overcast |
| Tue, Nov 17 | 54 °F | 37 °F | Overcast |
| Wed, Nov 18 | 54 °F | 39 °F | Overcast |
| Thu, Nov 19 | 48 °F | 35 °F | Partly cloudy |
| Fri, Nov 20 | 45 °F | 33 °F | Overcast |
| Sat, Nov 21 | 47 °F | 33 °F | Overcast |
Weather data by Open-Meteo.com · averages, not a forecast
Where to stay in New York City
Pod 51 is our best-value pick and the hotel in the total. It's $1,600 for the 7 nights ($229 a night) and scores 8.2 from 9,513 reviews, with free cancellation, but the room is a Bunk Pod with Shared Bathroom. Pod Times Square is our budget pick at $1,792 for the stay ($256 a night). It scores 8.6 from 16,599 reviews and has free cancellation and a Bunk Pod room. The Jewel Hotel, New York is the top-rated pick, a 4-star hotel at 8.8 from 2,655 reviews, costing $3,046 for the stay ($435 a night), with no free cancellation. All three are in Manhattan, with the room only. Midtown means Times Square, the Broadway theatres and the most hotel choice. The Upper West Side is quieter and sits next to Central Park and the museums.
Pod 51
$1,600 for 7 nights, two guests · $229 a night
See roomsThe Jewel Hotel, New York
$3,046 for 7 nights, two guests · $435 a night
See roomsPod Times Square
$1,792 for 7 nights, two guests · $256 a night
See roomsAll hotels in New York City for these dates
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Where in New York City
- Midtown: Times Square, Broadway theatres and the most hotel choice.
- SoHo / NoLIta: Boutique hotels amid cast-iron streets, shops and restaurants.
- Upper West Side: Quieter residential blocks next to Central Park and museums.
- Williamsburg, Brooklyn: Rooftop bars and skyline views one subway stop from Manhattan.
- Lower Manhattan: Weekend rates near the 9/11 Memorial, ferries and the Brooklyn Bridge.
What to do in New York City
- Walk through Times Square, then see a Broadway show
- Walk the High Line down to Chelsea Market
- Take the Staten Island Ferry past the Statue of Liberty
- Spend a morning at the Met or MoMA
- Cross the Brooklyn Bridge on foot at sunset
- Watch the sunset from Top of the Rock
Tours and tickets in New York City
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Getting there and around
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
|---|---|
| Airports in New York City | John F. Kennedy International (JFK), Newark Liberty International (EWR), LaGuardia (LGA) |
| Flight time | 9h 30m (1 stop) |
| Distance | 711 miles each way |
| Time difference | +1 hour |
What 7 nights in New York City costs
| Estimate | |
|---|---|
| Flights for two | $488 |
| Hotel, 7 nights (Pod 51) | $1,600 |
| Food, getting around and tickets, 7 days for two | $2,660 |
| Total for two | $4,748 |
Flights and hotel are the prices we found; spending is a planning estimate for a luxury destination, per person per day times two.
Price history: Chicago to New York City
| Per person | |
|---|---|
| This trip | $244 per person |
| Lowest in the last 30 days | $244 (Oct 14, 2026) |
| Typical price, last 60 days | $348 |
| Price checks | 19 |
Good to know
- Passport: no passport needed for travelers from the United States: a government photo ID is enough for New York City.
- Currency: US dollar (USD).
- Macy's Thanksgiving Day Parade and the NYC Marathon
- No passport needed, and the currency is the US dollar.
- New York is 1 hour ahead of Chicago.
- The Frontier flight leaves O'Hare at 10:29 AM and lands at 8:59 PM local time, with one stop.
- New York has three airports: JFK, Newark Liberty (EWR) and LaGuardia (LGA).
- Prices include taxes and fees as of when we checked; resort fees and a checked bag are extra.
Questions readers ask
Is it worth it?
Yes, if a one-stop travel day works for you. The fare is $244 per person, $104 below the typical fare on this route, and the week comes to $2,088 for two. If you want the shortest trip there, the stop is the cost of that price.
How much is the whole trip for two?
$2,088, all in: $488 for the Frontier flights and $1,600 for 7 nights at Pod 51, taxes and fees included. Resort fees, a checked bag and spending money aren't included. With our $190 per person a day for spending, the week comes to $4,748.
Is there a nonstop?
Yes. United has nonstops at 5:00 AM and 6:00 AM that take 2h 7m, at $273 per person or $546 for two. The Frontier fare has one stop and takes 9h 30m.
Do I need a passport?
No. It's a domestic trip from Chicago, and you'll be paying in US dollars. New York is just 1 hour ahead.
What is the weather like?
Typical highs are 45–55°F, with lows near 36°F, and most days are overcast. Pack a warm coat for ferry rides, bridge walks and the High Line.
Is 7 nights enough?
It's enough for the main sights at an easy pace: a Broadway show, the Met or MoMA, the Brooklyn Bridge, the Staten Island Ferry and Top of the Rock, with time left over to just wander.
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