$225 Find Cheap Flights from Simpson Bay to Illinois

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Simpson Bay to Illinois departing on 5/16. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Illinois

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Simpson Bay to Illinois, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Simpson Bay to Illinois, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% 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.

Best Illinois Flight Deals from Simpson Bay

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Chicago
Chicago2 stops$403

Cheap Flights from Simpson Bay to Illinois

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Simpson Bay to Illinois 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.

Recent round-trip flight deals from Simpson Bay to Illinois

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Simpson Bay to Illinois.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
Frontier Logo
6:15 pm - 12:17 amSXM-ORD
31h 02m2 stops
Frontier Logo
5:14 pm - 11:24 amORD-SXM
17h 10m1 stop
$403Frontier
Find Deal
Fri, May 23 - Fri, May 30
Frontier Logo
6:15 pm - 9:00 amSXM-MDW
39h 45m2 stops
Frontier Logo
9:12 pm - 11:24 amMDW-SXM
13h 12m1 stop
$410Frontier
Find Deal
Fri, May 23 - Fri, May 30
Spirit Airlines Logo
3:05 pm - 8:50 amSXM-ORD
18h 45m1 stop
Spirit Airlines Logo
12:41 pm - 2:00 pmORD-SXM
24h 19m1 stop
$466Spirit Airlines
Find Deal
Fri, May 23 - Fri, May 30
Spirit Airlines Logo
3:05 pm - 12:42 pmSXM-ORD
22h 37m3 stops
Spirit Airlines Logo
5:20 pm - 2:00 pmORD-SXM
19h 40m3 stops
$595Spirit Airlines
Find Deal
Fri, May 23 - Fri, May 30
Delta Logo
3:19 pm - 11:58 pmSXM-ORD
9h 39m1 stop
Delta Logo
5:30 am - 1:54 pmORD-SXM
7h 24m1 stop
$613Delta
Find Deal
Tue, May 20 - Tue, May 27
American Airlines Logo
4:10 pm - 11:57 pmSXM-ORD
8h 47m1 stop
American Airlines Logo
6:57 am - 3:10 pmORD-SXM
7h 13m1 stop
$620American Airlines
Find Deal
Thu, Oct 9 - Wed, Oct 15
American Airlines Logo
2:40 pm - 10:34 pmSXM-ORD
8h 54m1 stop
American Airlines Logo
6:00 am - 3:10 pmORD-SXM
8h 10m1 stop
$622American Airlines
Find Deal
Thu, Oct 9 - Wed, Oct 15
American Airlines Logo
3:24 pm - 11:56 pmSXM-ORD
9h 32m1 stop
American Airlines Logo
5:00 am - 3:31 pmORD-SXM
9h 31m2 stops
$627American Airlines
Find Deal
Tue, May 20 - Tue, May 27
 Logo
6:45 pm - 5:41 pmSXM-ORD
23h 56m3 stops
 Logo
5:51 am - 8:12 amORD-SXM
25h 21m3 stops
Tue, May 20 - Tue, May 27
Delta Logo
3:19 pm - 3:20 pmSXM-MDW
25h 01m1 stop
Delta Logo
6:00 am - 1:54 pmMDW-SXM
6h 54m1 stop
$886Delta
Find Deal
Fri, May 23 - Fri, May 30

KAYAK's insights & trends for Simpson Bay to Illinois flights

Get data-powered insights and trends into flights from Simpson Bay to Illinois to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Simpson Bay to Illinois flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Simpson Bay to Illinois.
The cheapest ticket to Illinois from Simpson Bay found in the last 72 hours was to Chicago, at $735 round-trip. The most popular route is from Simpson Bay (SXM) to Chicago O'Hare Intl Airport (ORD), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $735.

What is the cheapest time of day to fly to Illinois?

The average price for all round-trip flights from Simpson Bay to Illinois depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.
The cheapest time of day to fly to Illinois is generally in the afternoon, when round-trip flights cost $462 on average. Morning departures are around 100% cheaper than evening flights, on average. The most expensive time of day to fly to Illinois is generally in the evening, which is peak travel time and where the average cost of a ticket is $614.

Can I save money by flying with a layover from Simpson Bay to Illinois?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.
No, with an average price for the route of $610, prices are generally cheapest when you fly direct.

What’s the cheapest day of the week to fly from Simpson Bay to Illinois?

The average price of all round-trip flights from Simpson Bay to Illinois clicked on KAYAK for each day over the last 12 months.
For Simpson Bay to Illinois, Monday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Illinois back to Simpson Bay, the best deals are generally found on Monday, with Saturday being the most expensive.

Good to know

Cheapest flight

$225
Flight from Simpson Bay to Chicago O'Hare Airport

FAQs - booking Illinois flights

  • How does KAYAK find such low prices on flights from Simpson Bay to Illinois?

    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 from Simpson Bay to Illinois.

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

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

  • What is the Hacker Fare option on flights from Simpson Bay to Illinois?

    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 from Simpson Bay to Illinois 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 from Simpson Bay to Illinois?

    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 from Simpson Bay to Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top airline flying from Simpson Bay to Illinois

 
See real verified KAYAK customer reviews for airlines flying from Simpson Bay to Illinois. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Simpson Bay to Illinois? 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.
7.2
American AirlinesOverall score based on 10000 reviews
6.9Entertainment
7.2Comfort
8.0Crew
7.5Boarding
6.5Food
Airline reviews

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

2.0 MediocreAnonymous, Apr 2025SDF - ORD
Read more American Airlines reviews

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The flight was late and we missed this connecting flight. American Airlines refused to put us anywhere for the night for their snafu. We had to find our own accommodations in Miami, and it was expensive for a crappy hotel.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

My seat was horrible. I think it was broken in several places. Other than that, the crew was great and the plane was clean

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

Everything was on time, we arrived early, everything worked well.

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Everything you need to know for your flight from Simpson Bay to Illinois

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.