$421+ Cheap flights from Midway (MDW) to Singapore
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SIN
Nov 26 — Dec 31
1 adult, Economy
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Cheapest flights from Midway to SingaporeExplore the most affordable flight options available from Midway to Singapore. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 27, 2025.
Explore the most affordable flight options available from Midway to Singapore. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 27, 2025.
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/16:00 amMDW - SIN
2 stops33h 00mDelta
Mon 12/810:30 pmSIN - MDW
2 stops32h 04mDelta
Deal found 10/25![Delta logo]()
$1,384
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/26:00 amMDW - SIN
2 stops33h 00mDelta
Mon 12/1510:30 pmSIN - MDW
2 stops27h 25mDelta
Deal found 10/25![Delta logo]()
$1,463
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/96:00 amMDW - SIN
2 stops33h 00mDelta
Sat 11/2210:30 pmSIN - MDW
2 stops27h 22mDelta
Deal found 10/26![Delta logo]()
$1,484
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/76:00 amMDW - SIN
2 stops33h 00mDelta
Sat 11/2210:30 pmSIN - MDW
2 stops27h 22mDelta
Deal found 10/26![Delta logo]()
$1,509
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/276:00 amMDW - SIN
2 stops33h 00mDelta
Thu 12/410:30 pmSIN - MDW
2 stops27h 25mDelta
Deal found 10/27![Delta logo]()
$1,554
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/86:00 amMDW - SIN
2 stops33h 00mDelta
Mon 12/1510:30 pmSIN - MDW
2 stops27h 25mDelta
Deal found 10/25![Delta logo]()
$1,558
This KLM deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/85:29 pmMDW - SIN
2 stops32h 46mKLM
Sun 12/141:40 amSIN - MDW
2 stops28h 54mKLM
Deal found 10/26![KLM logo]()
$1,581
This KLM deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/95:29 pmMDW - SIN
2 stops32h 46mKLM
Mon 12/151:40 amSIN - MDW
2 stops29h 04mKLM
Deal found 10/25![KLM logo]()
$1,583
This Air France deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/275:34 pmMDW - SIN
2 stops33h 21mMultiple Airlines
Wed 12/31:40 amSIN - MDW
2 stops28h 38mMultiple Airlines
Deal found 10/27![Multiple Airlines logo]()
$1,587
This KLM deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/295:34 pmMDW - SIN
2 stops32h 41mKLM
Thu 12/41:40 amSIN - MDW
2 stops28h 38mKLM
Deal found 10/27![KLM logo]()
$1,593
Cheap flight deals from Midway to Singapore
Keep the following information in mind while searching for Midway to Singapore flight deals. Data was last updated October 27, 2025.
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $1,138 (Delta) |
One-way from | $421 (Kiwi.com) |
Popular in | December |
Cheapest in | February |
Average price | $902 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Singapore that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 27, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Singapore that are best for you.
Fly from
Midway
Fly to
Singapore
Route
Depart
Return
Price
ChicagoSingapore
MDW - SIN
MDWSIN
Chicago Midway
Mon 2/9
6:00 am-5:00 am
2 stops33h 00m
Singapore Changi
Sat 3/7
1:35 am-8:46 pm
2 stops33h 11m
$1,188
ChicagoSingapore
MDW - SIN
MDWSIN
Chicago Midway
Sat 1/17
5:25 pm-12:10 am
2 stops40h 45m
Singapore Changi
Tue 1/27
1:35 am-9:46 pm
2 stops34h 11m
$1,189
ChicagoSingapore
MDW - SIN
MDWSIN
Chicago Midway
Sun 1/18
5:25 pm-12:10 am
2 stops40h 45m
Singapore Changi
Thu 1/29
1:35 am-9:46 pm
2 stops34h 11m
$1,194
ChicagoSingapore
MDW - SIN
MDWSIN
Chicago Midway
Sun 4/12
9:20 am-7:55 pm
2 stops45h 35m
Singapore Changi
Wed 4/15
10:30 pm-8:38 am
2 stops47h 08m
$1,195
ChicagoSingapore
MDW - SIN
MDWSIN
Chicago Midway
Sat 4/11
6:10 pm-12:35 pm
2 stops29h 25m
Singapore Changi
Mon 4/20
1:45 pm-5:40 am
2 stops28h 55m
$1,247
ChicagoSingapore
MDW - SIN
MDWSIN
Chicago Midway
Thu 1/22
2:10 pm-1:05 pm
2 stops32h 55m
Singapore Changi
Tue 2/3
2:25 pm-12:40 pm
2 stops36h 15m
$1,249
ChicagoSingapore
MDW - SIN
MDWSIN
Chicago Midway
Sat 3/28
6:20 pm-12:35 pm
2 stops29h 15m
Singapore Changi
Sun 4/5
1:45 pm-11:10 am
2 stops34h 25m
$1,256
ChicagoSingapore
MDW - SIN
MDWSIN
Chicago Midway
Wed 1/14
5:31 pm-12:10 am
2 stops40h 39m
Singapore Changi
Fri 1/30
10:30 pm-10:26 pm
2 stops37h 56m
$1,284
ChicagoSingapore
MDW - SIN
MDWSIN
Chicago Midway
Wed 11/19
1:56 pm-2:00 pm
3 stops58h 04m
$439
ChicagoSingapore
MDW - SIN
MDWSIN
Chicago Midway
Thu 1/8
9:07 pm-5:45 pm
2 stops54h 38m
$475
Showing 1-10 of 19 results
Best time to book a flight from Midway to Singapore
Have a flexible travel schedule? Discover the best time to fly to Singapore from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago Midway Airport to Singapore
What is the cheapest time of day to fly from MDW to SG?
Find hourly flight availability from Midway to Singapore. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 27, 2025.
It’s typically best to fly out from Chicago Midway Airport to Singapore at noon. Doing so could potentially save you 31% on the flight price compared to flying in the morning, which is usually more expensive.