Cheap flights from Charlotte Amalie to Chicago

Cyril E. King
STT
Chicago FSS
CHI

Flight deals from Charlotte Amalie to Chicago

Below you can see the best deals on flights Charlotte Amalie — Chicago for upcoming dates. Direct and connecting flights from various airlines — compare prices and choose the right ticket.

The lowest price for the next 2 months is on 2 September, from $266.

Top 10 cheap flights from Charlotte Amalie to Chicago

B6
F9
$ 264

Charlotte Amalie — Chicago

15:45—23:27
2 Sep 2026
32 h 42 m
1 stop
B6
F9
$ 264

Charlotte Amalie — Chicago

15:45—23:27
3 Sep 2026
8 h 42 m
1 stop
B6
F9
$ 266

Charlotte Amalie — Chicago

15:48—23:27
5 Sep 2026
8 h 39 m
1 stop
B6
F9
$ 266

Charlotte Amalie — Chicago

15:45—23:27
3 Sep 2026
56 h 42 m
1 stop
B6
F9
$ 286

Charlotte Amalie — Chicago

15:45—23:27
2 Sep 2026
8 h 42 m
1 stop
B6
F9
$ 287

Charlotte Amalie — Chicago

15:45—23:27
1 Sep 2026
56 h 42 m
1 stop
B6
F9
B6
$ 298

Charlotte Amalie — Chicago

15:00—23:08
14 Sep 2026
33 h 8 m
2 stops
B6
F9
F9
$ 299

Charlotte Amalie — Chicago

15:00—15:20
11 Sep 2026
25 h 20 m
2 stops
B6
F9
F9
F9
$ 308

Charlotte Amalie — Chicago

15:00—20:29
14 Sep 2026
30 h 29 m
3 stops
B6
F9
$ 310

Charlotte Amalie — Chicago

15:59—23:27
4 Sep 2026
32 h 28 m
1 stop

Prices were found in the last 72 hours and may change — check the exact price when you continue.

About the Charlotte Amalie — Chicago flight

Looking for cheap flights from Charlotte Amalie to Chicago? Compare fares from different airlines, check the flight schedule and travel time — and book your Charlotte Amalie — Chicago ticket online at the best price.

The route has direct flights — around 17 flights per week, flights are operated by United Airlines, American Airlines, a nonstop flight takes about 7 h 46 min, the distance between the cities is around 3,383 km.

Planning your trip? You may find our Chicago travel guide, how to get from the airport into town and Chicago weather forecast useful. To catch a low fare, use the low-price calendar and the monthly price chart on this page.

Facts about this route

from $266Min. price
SeptemberCheapest
AugustPeak season
YesDirect flights
3,383 kmDistance
7 h 46 minTravel time
2Airlines
17 / wkFlights

Flight ticket prices by day: Charlotte Amalie — Chicago

Below is a calendar of the lowest flight ticket prices for Charlotte Amalie — Chicago by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from $266 in September, and the most expensive are around $335 in August. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.

 
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Prices by month

Average one-way fares from Charlotte Amalie to Chicago by month. Tickets are usually cheapest in September (around $288) and priciest in December (about $480) — use the table and chart below to pick the best time to fly.

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
Jan$456highMay$348mediumSep$288low
Feb$420highJun$396highOct$324low
Mar$432highJul$408highNov$348medium
Apr$372mediumAug$312lowDec$480high

Some values are estimated based on seasonality.

When to fly

Weather in Chicago: it is warmest in July (up to 27 °C on average) and coolest in January (around 0 °C). The driest month is November.

Tickets are usually cheapest in September and most expensive in August. Compare prices and weather by month in the charts below to pick the best time to fly.

Temperature · Chicago

Dry and wet days · Chicago

Wind speed and direction · Chicago

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How to get the best deal on a Charlotte Amalie — Chicago ticket

  • Book ahead: fares for Charlotte Amalie — Chicago are usually lower 3–8 weeks before departure than at the last minute.
  • Play with your dates — Tuesday, Wednesday and Saturday departures are often cheaper than Friday and Sunday.
  • The cheapest month to fly to Chicago is usually September — plan your trip around it if your dates are flexible.
  • Compare direct and connecting flights: nonstop is faster, while a connection is sometimes noticeably cheaper.
  • Watch the low-price calendar and the monthly price trend on this page — they make it easier to catch a good date.
  • Travelling light? Pick a cabin-baggage-only fare — tickets without checked luggage are noticeably cheaper.
  • Get to the airport in good time — about 2–3 hours before an international departure and roughly an hour before a domestic one.

Airlines

Flights on the Charlotte Amalie — Chicago route are operated by 2 airlines; United Airlines runs the most flights (around 65% of all flights). Compare carriers, flight shares and schedules below.

  • United AirlinesUA
    4x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight STT → ORD4x/week
    64.7%Open →
  • American AirlinesAA
    2x/week
    WebsiteFleet: 965211M pax/year
    • Direct flight STT → ORD2x/week
    35.3%Open →

Cities and airports on the Charlotte Amalie — Chicago route

Flights Charlotte Amalie — Chicago depart from Cyril E. King Airport and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.

Departure

Charlotte Amalie

STT
U.S. Virgin Islands
About the cityHow to get thereWeatherAll about the country U.S. Virgin Islands
Arrival

Chicago

CHI
United States
About the cityHow to get thereWeatherAll about the country United States
Departure airports
Arrival airports

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Frequently asked questions about the Charlotte Amalie — Chicago flight

How long is the flight from Charlotte Amalie to Chicago?

A nonstop Charlotte Amalie — Chicago flight takes about 7 h 46 min — the distance between the cities is around 3,383 km.

How far is it from Charlotte Amalie to Chicago?

The distance from Charlotte Amalie to Chicago is about 3,383 km, which a nonstop flight covers in around 7 h 46 min.

Are there direct flights from Charlotte Amalie to Chicago?

Yes, there are nonstop flights Charlotte Amalie — Chicago — around 17 flights per week.

Which airlines fly from Charlotte Amalie to Chicago?

Airlines operating Charlotte Amalie — Chicago include United Airlines, American Airlines. See the full list with schedules in the "Airlines" section on this page.

Which airports do Charlotte Amalie — Chicago flights use?

Flights from Charlotte Amalie depart from Cyril E. King Airport, and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport. If a city has more than one airport, check which one your ticket uses before you travel.

How much is a ticket from Charlotte Amalie to Chicago?

The price of a Charlotte Amalie — Chicago ticket depends on your travel date, season and demand: it is usually cheapest to fly in September, and most expensive in August. Tickets typically cost between $266 and $335. Check the current lowest fare and low-price calendar on this page.

When is the best time to book flights Charlotte Amalie — Chicago?

Flights Charlotte Amalie — Chicago are usually cheaper when booked in advance — a few weeks before departure and away from peak dates; the most budget-friendly month to fly is September. Compare prices by month in the price trend chart on this page.

How can I find the cheapest flights from Charlotte Amalie to Chicago?

To catch a low fare Charlotte Amalie — Chicago, book a few weeks in advance, keep your dates flexible, and compare airlines and connecting options. The low-price calendar and monthly price chart on this page show the cheapest days and months at a glance: the most budget-friendly month to fly is usually September.

How early should I arrive at the airport?

For international flights, plan to be at the airport about 2–3 hours before departure, and around an hour before a domestic flight. Allow extra time during busy travel seasons and at large hubs, where check-in and security lines can be longer.

Where else you can fly from Charlotte Amalie

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San JuanNew York CityTortolaAtlantaCharlotteGustaviaWashington, D.C.OrlandoDallasFort LauderdaleHoustonBostonMiamiThe ValleyBasseterreDominicaCharlestownPhiladelphiaMinneapolisSaint CroixSanto DomingoBridgetownPanama CityLondonTorontoParisKingstonMadridCaracas

Where else you can fly from Chicago

See all
New York CityTorontoDetroitWashington, D.C.AtlantaMinneapolisLos AngelesSeattleBostonDallasHoustonOrlandoDenverLondonNashvilleIndianapolisSan DiegoMontrealMilwaukeeSt. LouisCharlottePhiladelphiaColumbusKansas CityPhoenixMiamiLas VegasCincinnatiGrand RapidsDes MoinesRaleighSan FranciscoMadisonDaytonGreen BayTampaPittsburghLouisvilleKnoxvilleRochester

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