$251 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 7/21. 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
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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

Fri, Jun 12 - Mon, Jun 15
JetBlue Logo
3:30 pm - 1:00 pm
STT
-
ORD
22h 30m
2 stops
JetBlue Logo
8:20 pm - 2:03 pm
ORD
-
STT
16h 43m
1 stop
$498JetBlue
Wed, Jul 22 - Mon, Jul 27
American Airlines Logo
4:50 pm - 11:30 pm
STT
-
ORD
7h 40m
1 stop
American Airlines Logo
5:07 am - 4:00 pm
ORD
-
STT
9h 53m
2 stops
$580American Airlines
Sat, Jun 20 - Mon, Jul 20
JetBlue Logo
2:00 pm - 10:01 am
STT
-
ORD
21h 01m
2 stops
JetBlue Logo
8:10 pm - 2:03 pm
ORD
-
STT
16h 53m
1 stop
$609JetBlue
Wed, Jun 24 - Wed, Jul 1
American Airlines Logo
4:49 pm - 9:09 am
STT
-
ORD
17h 20m
1 stop
American Airlines Logo
8:52 pm - 1:48 pm
ORD
-
STT
15h 56m
1 stop
$620American Airlines
Wed, Jul 22 - Mon, Jul 27
American Airlines Logo
1:49 pm - 11:30 pm
STT
-
ORD
10h 41m
2 stops
American Airlines Logo
5:07 am - 4:00 pm
ORD
-
STT
9h 53m
2 stops
$665American Airlines
Fri, Jun 12 - Mon, Jun 15
JetBlue Logo
3:30 pm - 1:00 pm
STT
-
ORD
22h 30m
2 stops
JetBlue Logo
8:20 pm - 3:17 pm
ORD
-
STT
17h 57m
2 stops
$667JetBlue
Sat, Jul 25 - Thu, Jul 30
JetBlue Logo
2:00 pm - 10:05 am
STT
-
ORD
21h 05m
2 stops
JetBlue Logo
8:10 pm - 1:59 pm
ORD
-
STT
16h 49m
1 stop
$673JetBlue
Wed, Jul 1 - Sun, Jul 5
American Airlines Logo
3:46 pm - 9:08 am
STX
-
ORD
18h 22m
1 stop
American Airlines Logo
8:30 am - 8:50 pm
ORD
-
STX
11h 20m
1 stop
$681American Airlines
Wed, Jul 1 - Sun, Jul 5
American Airlines Logo
9:01 am - 12:33 am
STX
-
ORD
16h 32m
1 stop
American Airlines Logo
6:30 am - 8:50 pm
ORD
-
STX
13h 20m
2 stops
$685American Airlines
Sat, Jun 20 - Mon, Jul 20
United Airlines Logo
4:45 pm - 11:26 pm
STT
-
ORD
7h 41m
1 stop
United Airlines Logo
5:30 am - 3:43 pm
ORD
-
STT
9h 13m
1 stop
$695United 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 3 days.

In the last 3 days, the cheapest flight deal to Chicago was found on the route from Saint Thomas Island, at $498 return. The most popular connection is from New York to Chicago and KAYAK users have found round-trip deals for as low as $177 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 Sunday where round-trip tickets can be as cheap as $505. 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$251
Best time to beat the crowds with an average 13% 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 $498 return. The most popular connection is from New York to Chicago and KAYAK users have found round-trip deals for as low as $177 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 $392. The cheapest price found on KAYAK in the last 2 weeks cost $317 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 $327
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Reviews of the top airline 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 11630 reviews
6.9Entertainment
7.2Comfort
7.5Boarding
7.9Crew
6.4Food
Airline reviews

They lost my baggage and I am still struggling to the information and update

2.0 MediocrePrajakta, May 2026
DFW - ORD
Read more American Airlines reviews

They lost my baggage and I am still struggling to the information and update

The homeless eat better than what was served on that plane. Pretzels and ice cream? My last trip to Europe. Everything is small, but the bill.

Awful customer service, horrible experience. We travel a lot domestic & international- worst flights to/from ever. Brief bkgd as Inhate to relive this experience: booked and chose 2 seats 4 months prior in Premium Economy - last row end seats close to bathroom, no one behind us, plenty of legroom;, underwear storage — flown this was on other airlines, love it. We receive notice 4 days before scheduled overseas flight - plane has changed, new seats assigned. Seats are split into single seats, opposites of the plane, FRONT Row so no reachable storage. Called BOTH British Air & America. American “switched planes and the seats you want are taken;” British Air “Yes, we’ll be glad to accommodate you (type type type). Just ask at the Gate and someone will give you new boarding passes with seats together in middle, OK?” — OK. —At Gate the attendant looks us up saying “No, it is an overbooked flight and yours are the only seats available.” But but but wait, “We were TOLD our seats had been switched and seated together?” Gate attendant “Well they were wrong and don’t change your seats. Your original seats are where you’ll sit.”. Right. No help WHATSOEVER. We sit opposite on way there, wife VERY disgruntled, a Tol 5 worst ways to start a 3-week bus tour of UK. We promise to NEVER FLY AMERICAN OR BROTISH AIR EVER, and we have 3 more extensive trips planned..

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

The wifi experience is awful. I had to try again and again, taking over 30 minutes, to connect to the wifi. I had to watch the same two ads over and over until I was finally successful. Once connected, it was anything but "high speed" and disconnected at least three times during the flight.

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

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
Hammond
Elk Grove Village
Des Plaines
Hoffman Estates
Portage
Willowbrook
South Holland
Delavan
Lansing
Northbrook
Lisle
Elmhurst
Pleasant Prairie
Alsip

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

Information on the airport you'll fly into in Chicago