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$468+ 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 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SIN
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap flight deals from Midway to Singapore

Cheapest flights from Midway to Singapore
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 December 12, 2025.

This Delta deal was found by Cheapflights users on 12/10. 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 12/266:00 amMDW - SIN
2 stops33h 00mDelta
Sun 1/410:30 pmSIN - MDW
2 stops31h 59mDelta
Deal found 12/10$1,986
This Delta deal was found by Cheapflights users on 12/10. 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 12/256:00 amMDW - SIN
2 stops33h 00mDelta
Mon 1/510:30 pmSIN - MDW
2 stops31h 59mDelta
Deal found 12/10$2,035
This Delta deal was found by Cheapflights users on 12/10. 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 12/216:00 amMDW - SIN
2 stops33h 00mDelta
Sat 12/271:35 amSIN - MDW
2 stops34h 47mDelta
Deal found 12/10$2,062
This Delta deal was found by Cheapflights users on 12/10. 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 12/226:00 amMDW - SIN
2 stops33h 00mDelta
Mon 12/2910:30 pmSIN - MDW
2 stops27h 28mDelta
Deal found 12/10$2,328
This Delta deal was found by Cheapflights users on 12/10. 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.
Wed 12/246:00 amMDW - SIN
2 stops33h 00mDelta
Sun 1/410:30 pmSIN - MDW
2 stops31h 59mDelta
Deal found 12/10$2,336
This Delta deal was found by Cheapflights users on 12/10. 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 12/216:00 amMDW - SIN
2 stops33h 00mDelta
Fri 1/910:30 pmSIN - MDW
2 stops31h 59mDelta
Deal found 12/10$2,436
This Delta deal was found by Cheapflights users on 12/10. 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 12/236:00 amMDW - SIN
2 stops33h 00mDelta
Sat 1/310:40 amSIN - MDW
2 stops39h 18mDelta
Deal found 12/10$2,664
This Delta deal was found by Cheapflights users on 12/10. 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.
Sat 12/206:00 amMDW - SIN
2 stops33h 00mDelta
Fri 12/261:35 amSIN - MDW
2 stops34h 47mDelta
Deal found 12/10$2,996
This Air France deal was found by Cheapflights users on 12/10. 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.
Mon 12/226:08 pmMDW - SIN
2 stops32h 47mMultiple Airlines
Sat 12/271:40 amSIN - MDW
2 stops28h 40mMultiple Airlines
Deal found 12/10$3,157
This Air France deal was found by Cheapflights users on 12/10. 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.
Sun 12/216:08 pmMDW - SIN
2 stops24h 52mMultiple Airlines
Sun 12/281:40 amSIN - MDW
2 stops29h 39mMultiple Airlines
Deal found 12/10$3,232
This Delta deal was found by Cheapflights users on 12/10. 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.
Sat 12/206:00 amMDW - SIN
2 stops33h 00mDelta
Sun 1/410:30 pmSIN - MDW
2 stops37h 37mDelta
Deal found 12/10$3,320
This Air France deal was found by Cheapflights users on 12/9. 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.
Wed 12/101:50 pmMDW - SIN
2 stops29h 10mMultiple Airlines
Tue 12/161:40 amSIN - MDW
2 stops30h 20mMultiple Airlines
Deal found 12/9$3,399

Find flight deals from Midway to Singapore

Keep the following information in mind while searching for Midway to Singapore flight deals. Data was last updated December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$1,301
(Delta)

One-way from

$468
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$1,913
Provider with most accurate pricing for Chicago (CHI)-Singapore Changi flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Singapore Changi flights.
Search Deals
From Chicago Midway to Singapore
Search Deals
One-way flight from Chicago Midway to Singapore
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($211 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($71 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 12, 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

Wed 3/4

6:00 am-5:00 am

2 stops33h 00m

Singapore Changi

Sat 3/28

1:35 am-10:29 pm

2 stops33h 54m

$1,301

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Mon 1/26

10:35 am-1:05 pm

2 stops36h 30m

Singapore Changi

Mon 2/9

2:25 pm-12:40 pm

2 stops36h 15m

$1,320

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Fri 1/23

7:45 am-1:05 pm

2 stops39h 20m

Singapore Changi

Sat 1/31

2:25 pm-12:15 pm

2 stops35h 50m

$1,331

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Mon 2/9

3:40 pm-1:05 pm

3 stops31h 25m

Singapore Changi

Sat 3/7

3:00 am-8:45 pm

2 stops31h 45m

$1,442

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Fri 5/22

4:35 pm-12:35 pm

3 stops31h 00m

Singapore Changi

Sat 6/6

1:45 pm-5:40 am

2 stops28h 55m

$1,521

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Fri 1/23

6:14 pm-12:10 am

2 stops39h 56m

Singapore Changi

Sat 1/31

10:30 pm-11:59 am

2 stops27h 29m

$1,572

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Wed 3/4

11:10 am-1:05 pm

3 stops35h 55m

Singapore Changi

Sat 3/28

2:00 am-11:55 pm

2 stops34h 55m

$1,596

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Tue 1/6

6:45 am-5:00 am

2 stops32h 15m

Singapore Changi

Sun 1/18

10:30 pm-11:59 am

2 stops27h 29m

$1,636

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sun 1/18

6:30 pm-9:15 am

2 stops48h 45m

$468

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sun 1/25

5:01 pm-6:55 am

3 stops47h 54m

$492

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 17 results
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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 December 12, 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.

Related info for your journey

Find useful and relevant information for your journey from Midway to Singapore. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago Midway Airport to Singapore?

    Airlines like Delta fly from Chicago Midway Airport to Singapore in about 33h. The time it takes to get you to your destination can typically vary by up to . The distance between Chicago Midway Airport and Singapore is about 9360 mi.

  • Can I find deals for flights from Midway to Singapore that include hotel bookings?

    Yes. In addition to deals on Midway to Singapore flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Singapore?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Singapore.

  • Can I find deals for business class flights from Midway to Singapore?

    Yes. Cheapflights offers flight deals from Midway to Singapore by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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Alternative routes for Midway to Singapore

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