$142 Find Cheap Flights from U.S. Virgin Islands to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to O'Hare Intl departing on 4/14. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago O'Hare Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from the U.S. Virgin Islands to O'Hare Intl

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from the U.S. Virgin Islands to O'Hare Intl that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from the U.S. Virgin Islands to O'Hare Intl

Wed, Mar 25 - Mon, Mar 30
Spirit Airlines Logo
4:35 pm - 11:17 pm
STT
-
ORD
7h 42m
1 stop
Spirit Airlines Logo
6:10 pm - 3:28 pm
ORD
-
STT
20h 18m
1 stop
$329Spirit Airlines
Tue, Apr 28 - Sun, May 3
Spirit Airlines Logo
5:10 pm - 12:24 am
STT
-
ORD
8h 14m
1 stop
Spirit Airlines Logo
11:28 am - 1:09 pm
ORD
-
STT
24h 41m
2 stops
$333Spirit Airlines
Tue, Apr 28 - Sun, May 3
Spirit Airlines Logo
12:25 pm - 12:24 am
STT
-
ORD
12h 59m
1 stop
Spirit Airlines Logo
10:31 am - 9:54 am
ORD
-
STT
22h 23m
1 stop
$341Spirit Airlines
Wed, Mar 25 - Mon, Mar 30
Spirit Airlines Logo
4:35 pm - 11:17 pm
STT
-
ORD
7h 42m
1 stop
Spirit Airlines Logo
6:10 pm - 1:26 pm
ORD
-
STT
18h 16m
2 stops
$352Spirit Airlines
Wed, Mar 25 - Mon, Mar 30
Spirit Airlines Logo
4:35 pm - 11:17 pm
STT
-
ORD
7h 42m
1 stop
Spirit Airlines Logo
6:10 pm - 3:28 pm
ORD
-
STT
20h 18m
1 stop
$353Spirit Airlines
Thu, Mar 26 - Mon, Mar 30
Multiple Airlines Logo
2:36 pm - 11:38 pm
STT
-
ORD
10h 02m
1 stop
Multiple Airlines Logo
5:05 am - 3:28 pm
ORD
-
STT
9h 23m
1 stop
$395Multiple Airlines
Wed, Apr 1 - Tue, Apr 7
American Airlines Logo
1:50 pm - 12:06 am
STX
-
ORD
11h 16m
2 stops
American Airlines Logo
8:46 pm - 1:15 pm
ORD
-
STX
15h 29m
2 stops
$550American Airlines
Wed, Apr 1 - Wed, Apr 8
American Airlines Logo
1:50 pm - 12:06 am
STX
-
ORD
11h 16m
2 stops
American Airlines Logo
8:46 pm - 1:15 pm
ORD
-
STX
15h 29m
2 stops
$565American Airlines
Tue, May 5 - Sat, May 23
American Airlines Logo
5:14 pm - 11:04 am
STX
-
ORD
18h 50m
1 stop
American Airlines Logo
8:25 am - 8:41 pm
ORD
-
STX
11h 16m
1 stop
$571American Airlines
Tue, May 5 - Sat, May 23
American Airlines Logo
5:14 pm - 7:24 am
STX
-
ORD
15h 10m
2 stops
American Airlines Logo
8:25 am - 8:41 pm
ORD
-
STX
11h 16m
1 stop
$575American Airlines
Booking Insights

KAYAK's insights & trends for flights to O'Hare Intl

Get data-powered insights and trends for flights to O'Hare Intl to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest flight to Chicago?

These are the best round-trip prices found by users searching on KAYAK in the last 72 hours.

In the last 3 days, the cheapest flight deal to Chicago was found on the route from Saint Thomas Island, at $329 return. The most popular connection is from Boston to Chicago and KAYAK users have found round-trip deals for as low as $135 in the last 3 days.

What is the cheapest day to fly to Chicago?

The average price of all round-trip flights to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.

Based on KAYAK data, the cheapest day to fly to Chicago is Wednesday where round-trip tickets can be as cheap as $516. On the other hand, the most expensive day to fly is Friday, where round-trip prices are $801 on average.

What is the cheapest time of day to fly to Chicago O'Hare Intl Airport?

The average price for all round-trip flights to Chicago O'Hare Intl Airport depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Chicago O'Hare Intl Airport is generally in the afternoon, when round-trip flights cost $536 on average. The most expensive time of day to fly to Chicago O'Hare Intl Airport is generally in the evening, which is peak travel time and where the average cost of a ticket is $567.

Good to know

Low seasonDecember
Cheapest flight$142
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from Saint Thomas Island to Chicago

FAQs - booking Chicago flights

  • What is the cheapest flight to Chicago?

    In the last 3 days, the cheapest flight deal to Chicago was found on the route from Saint Thomas Island, at $329 return. The most popular connection is from Boston to Chicago and KAYAK users have found round-trip deals for as low as $135 in the last 3 days.

  • How far is Chicago O'Hare Intl Airport from central Chicago?

    Chicago O'Hare Intl Airport is 16 miles from the center of Chicago.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $357. The cheapest price found on KAYAK in the last 2 weeks cost $172 and departed from Saint Thomas Island Cyril E King Airport.

  • How does KAYAK find such low prices on flights to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Chicago

  • Looking for cheap airfare to Chicago? 25% of our users found round-trip tickets to Chicago for the following prices or less: From Saint Thomas Island $186
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Reviews of the top airlines flying from the U.S. Virgin Islands to O'Hare Intl

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from the U.S. Virgin Islands to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with to O'Hare Intl? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
American AirlinesOverall score based on 11464 reviews
7.5Boarding
6.9Entertainment
6.4Food
7.2Comfort
7.9Crew
Airline reviews

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

2.0 MediocreBrendan, Mar 2026
LGA - ORD
Read more American Airlines reviews

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

I understand that there is a catering issue - water should be the minimum stock. During the flight, not once that the attendants came through with water. The conversations in the kitchen were very loud and they were swearing. I do not expect any white glove service, at the minimum, we should be cordial. It was almost an inconveniece that we were on the flight. And it made us feel if you even dare question us, we'll make you deplane.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Waited for oxygen tanks for 30 minutes after boarding was complete.

For a change, friendly staff at check-in and in flight.

Delayed both in takeoff and landing, trash plane no amenities, I've said it before but I'll never fly Spirit again.

It’s was a cheap flight and they got us there safely. It’s just their whole business model that make the experience “meh.” They make you paranoid about whether your personal item is too big. They make you paranoid about being crammed into a middle seat at the back of the plane. They purposely cram people together leaving multiple rows completely empty and even after the door closes the FA’s announce that everyone has to sit in their assigned seat. We knew what we were buying and in that regard we got a cheap and safe flight but it felt like they do their best to take any enjoyment out of the experience. That’s all on management, not the crew.

Had to pay for my bag a mini weekender bag 100 dollar fee

The flight was delayed for unknown reasons while other airlines weren’t. It was very frustrating.

Everything was good. On time, boarding fast, flight attendants friendly.

Spirit has always and will always stink. Absolute worst airline around.

Not seat assigned because overbooking. We could go because some people decided to give their seats.

The flights were very uncomfortable the seats don't have much leg room at all and they are pretty hard as well.

Our outgoing flight was cancelled two hours before boarding and Spirit was not able to get us onto another flight. Their customer service was slow and unhelpful.

Traveling to a place near O'Hare Intl?

Book flights to O'Hare Intl if you plan to visit one of these locations
Gurnee
South Haven
Merrillville
Oak Brook
Saint Joseph
Tinley Park
Elk Grove Village
Des Plaines
Hammond
Hoffman Estates
Willowbrook
Portage
South Holland
Delavan
Northbrook
Lansing
Pleasant Prairie
Lisle
Elmhurst
Valparaiso

Everything you need to know for your flight to O'Hare Intl

Information on the airport you'll fly into in Chicago