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Cheap flights from Singapore to Chicago Midway Airport from S$ 723
This is the cheapest retur flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10-11. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — MDW
12 Nov — 19 Nov1
Cheap flight deals from Singapore to Midway
Enter your travel dates to find the best prices.
Cheapest
Best
Last-minute
One-way
Cheapest flights from Singapore to MidwayExplore the most affordable flight options available from Singapore to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 13 October 2026.
Explore the most affordable flight options available from Singapore to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 13 October 2026.
Tue 10-1122:30 -
2 stops27h 29m
Tue 17-1106:00 -
2 stops33h 00m
Deal found 13-10S$ 1,226
Tue 10-1101:40 -
2 stops35h 14m
Wed 25-1106:00 -
2 stops33h 00m
Deal found 12-10S$ 1,259
Mon 23-1122:30 -
2 stops31h 48m
Mon 30-1106:00 -
2 stops33h 00m
Deal found 9-10S$ 1,388
Tue 1-1222:30 -
2 stops31h 46m
Tue 8-1206:00 -
2 stops33h 00m
Deal found 11-10S$ 1,518
Wed 14-1013:55 -
2 stops28h 55m
Wed 28-1010:30 -
2 stops37h 35m
Deal found 12-10S$ 1,620
Sun 8-1114:25 -
2 stops34h 55m
Sun 15-1116:45 -
2 stops30h 20m
Deal found 9-10S$ 1,625
Fri 30-1014:25 -
2 stops34h 30m
Sun 15-1116:45 -
2 stops30h 20m
Deal found 12-10S$ 1,636
Thu 22-1022:00 -
2 stops31h 14m
Sun 25-1006:04 -
2 stops33h 56m
Deal found 9-10S$ 1,667
Fri 23-1013:55 -
2 stops34h 40m
Mon 26-1015:55 -
2 stops32h 10m
Deal found 9-10S$ 1,676
Best flights from Singapore to MidwayDiscover carefully curated flight deals from Singapore to Midway that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 13 October 2026.
Discover carefully curated flight deals from Singapore to Midway that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 13 October 2026.
Tue 10-1122:30 -
2 stops27h 29m
Tue 17-1106:00 -
2 stops33h 00m
Deal found 13-10S$ 1,226
Fri 30-1014:25 -
2 stops34h 30m
Sun 15-1116:45 -
2 stops30h 20m
Deal found 12-10S$ 1,636
Tue 24-1122:30 -
2 stops31h 48m
Tue 1-1206:00 -
2 stops33h 00m
Deal found 10-10S$ 1,259
Tue 10-1101:40 -
2 stops35h 14m
Wed 25-1106:00 -
2 stops33h 00m
Deal found 12-10S$ 1,259
Tue 26-114:25 -
2 stops36h 00m
Tue 2-215:50 -
3 stops31h 15m
Deal found 9-10S$ 1,649
Mon 23-1122:30 -
2 stops31h 48m
Mon 30-1106:00 -
2 stops33h 00m
Deal found 9-10S$ 1,388
Fri 23-1013:55 -
2 stops34h 40m
Mon 26-1015:55 -
2 stops32h 10m
Deal found 9-10S$ 1,676
Wed 10-222:30 -
2 stops31h 55m
Wed 24-206:00 -
2 stops33h 00m
Deal found 9-10S$ 1,390
Tue 1-1222:30 -
2 stops31h 46m
Tue 8-1206:00 -
2 stops33h 00m
Deal found 8-10S$ 1,520
Tue 24-1113:15 -
3 stops32h 57m
Tue 1-1212:28 -
3 stops33h 37m
Deal found 10-10S$ 1,956
Sun 8-1122:30 -
2 stops27h 29m
Thu 12-1106:00 -
2 stops33h 00m
Deal found 11-10S$ 2,006
Last-minute flights from Singapore to MidwayDiscover last-minute flight deals from Singapore to Midway. Data last updated 13 October 2026 and is based on user searches.
Discover last-minute flight deals from Singapore to Midway. Data last updated 13 October 2026 and is based on user searches.
Wed 14-1013:55 -
2 stops28h 55m
Wed 28-1010:30 -
2 stops37h 35m
Deal found 12-10S$ 1,620
Sun 18-1013:55 -
2 stops29h 10m
Sun 25-1018:30 -
2 stops29h 35m
Deal found 12-10S$ 1,677
Thu 22-1022:00 -
2 stops31h 14m
Sun 25-1006:04 -
2 stops33h 56m
Deal found 9-10S$ 1,667
Fri 23-1013:55 -
2 stops34h 40m
Mon 26-1015:55 -
2 stops32h 10m
Deal found 9-10S$ 1,676
Fri 30-1014:25 -
2 stops34h 30m
Sun 15-1116:45 -
2 stops30h 20m
Deal found 12-10S$ 1,636
Sun 8-1114:25 -
2 stops34h 55m
Sun 15-1116:45 -
2 stops30h 20m
Deal found 9-10S$ 1,625
Tue 10-1122:30 -
2 stops27h 29m
Tue 17-1106:00 -
2 stops33h 00m
Deal found 13-10S$ 1,226
Tue 10-1101:40 -
2 stops35h 14m
Wed 25-1106:00 -
2 stops33h 00m
Deal found 12-10S$ 1,259
Mon 23-1122:30 -
2 stops31h 48m
Mon 30-1106:00 -
2 stops33h 00m
Deal found 9-10S$ 1,388
One-way flights from Singapore to MidwaySearch for one-way flight options from Singapore to Midway. Find affordable one-way fares based on user searches. Data last updated 13 October 2026.
Search for one-way flight options from Singapore to Midway. Find affordable one-way fares based on user searches. Data last updated 13 October 2026.
Tue 10-1110:30 -
2 stops26h 24m
Wed 31-1200:00 -
Nonstop0h 00m
Deal found 11-10S$ 723
Mon 18-122:30 -
2 stops37h 40m
Wed 31-1200:00 -
Nonstop0h 00m
Deal found 9-10S$ 726
Mon 11-101:40 -
2 stops34h 30m
Wed 31-1200:00 -
Nonstop0h 00m
Deal found 12-10S$ 796
Sun 20-1219:25 -
2 stops49h 36m
Wed 31-1200:00 -
Nonstop0h 00m
Deal found 9-10S$ 851
Tue 10-1123:10 -
3 stops56h 37m
Wed 31-1200:00 -
Nonstop0h 00m
Deal found 11-10S$ 853
Sun 6-1222:30 -
2 stops33h 31m
Wed 31-1200:00 -
Nonstop0h 00m
Deal found 10-10S$ 927
Sun 13-1223:10 -
3 stops50h 23m
Wed 31-1200:00 -
Nonstop0h 00m
Deal found 11-10S$ 938
Sat 5-1220:45 -
3 stops56h 10m
Wed 31-1200:00 -
Nonstop0h 00m
Deal found 10-10S$ 960
Find flight deals from Singapore to Midway
Discover tips and strategies to find the most affordable flight options for your journey from Singapore (SIN) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 13 October 2026.
Cheapflights Fare Finder
Customise your flight search to find flights from Singapore to Midway 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 7,457,451 searches. Data last updated 13 October 2026.
Use the filters below to find and compare flights from Singapore to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest return flight
Fastest return journey
SingaporeChicago
SIN Singapore Changi - MDW Chicago Midway
SINMDW
Singapore Changi
Tue 10-11
10:30-22:54
2 stops26h 24m
Chicago Midway
Wed 31-12
00:00-13:30
Nonstop0h 00m
S$ 723
SingaporeChicago
SIN Singapore Changi - MDW Chicago Midway
SINMDW
Singapore Changi
Mon 11-1
01:40-22:10
2 stops34h 30m
Chicago Midway
Wed 31-12
00:00-13:30
Nonstop0h 00m
S$ 796
SingaporeChicago
SIN Singapore Changi - MDW Chicago Midway
SINMDW
Singapore Changi
Sun 13-12
14:25-06:05
2 stops29h 40m
Chicago Midway
Wed 31-12
00:00-13:30
Nonstop0h 00m
S$ 955
SingaporeChicago
SIN Singapore Changi - MDW Chicago Midway
SINMDW
Singapore Changi
Fri 19-3
10:30-08:49
2 stops35h 19m
Chicago Midway
Wed 31-12
00:00-13:30
Nonstop0h 00m
S$ 973
SingaporeChicago
SIN Singapore Changi - MDW Chicago Midway
SINMDW
Singapore Changi
Fri 19-3
14:25-06:00
2 stops28h 35m
Chicago Midway
Wed 31-12
00:00-13:30
Nonstop0h 00m
S$ 977
SingaporeChicago
SIN Singapore Changi - MDW Chicago Midway
SINMDW
Singapore Changi
Sat 5-12
14:25-11:20
2 stops34h 55m
Chicago Midway
Wed 31-12
00:00-13:30
Nonstop0h 00m
S$ 981
SingaporeChicago
SIN Singapore Changi - MDW Chicago Midway
SINMDW
Singapore Changi
Tue 10-11
22:30-11:59
2 stops27h 29m
Chicago Midway
Tue 17-11
06:00-05:00
2 stops33h 00m
S$ 1,226
SingaporeChicago
SIN Singapore Changi - MDW Chicago Midway
SINMDW
Singapore Changi
Tue 24-11
22:30-16:18
2 stops31h 48m
Chicago Midway
Tue 1-12
06:00-05:00
2 stops33h 00m
S$ 1,259
SingaporeChicago
SIN Singapore Changi - MDW Chicago Midway
SINMDW
Singapore Changi
Tue 10-11
01:40-22:54
2 stops35h 14m
Chicago Midway
Wed 25-11
06:00-05:00
2 stops33h 00m
S$ 1,259
SingaporeChicago
SIN Singapore Changi - MDW Chicago Midway
SINMDW
Singapore Changi
Mon 23-11
22:30-16:18
2 stops31h 48m
Chicago Midway
Mon 30-11
06:00-05:00
2 stops33h 00m
S$ 1,388
Showing 1-10 of 17 resultsSorted by cheapest first
Best time to book a flight from Singapore to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Singapore with our price prediction graph.
SIN-MDW
Estimated return 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.
Related info for your journey
Find useful and relevant information for your journey from Singapore to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
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Popular flights
Alternative routes for Singapore to Midway
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Midway by adding a car rental and/or hotel reservation to your travel itinerary.
Direct flights to United States
Book a non-stop flight to one of these other cities located in United States.
Search flights from Singapore to Midway by cabin class
Find flights from Singapore to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Singapore and Midway flights
Browse other Singapore and Midway flight options. Last updated on 13 October 2026.
Popular flight searches
Check out other popular destinations found by fellow travellers in 2026
Fly with Cheapflights
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How does Cheapflights help users find flights from Singapore to Midway?
Cheapflights makes it easy to find Singapore to Midway flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.
Why should you use Cheapflights to find cheap flight tickets from Singapore to Midway?
By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Midway from Singapore.
Can Cheapflights find flights from Singapore to Midway with no change fees?
Cheapflights does show flights with no change fees to all users. To see these options for flights from Singapore to Midway, users can toggle the no change fees filter when performing a flight search.
Can Cheapflights notify me if prices for flights from Singapore to Midway become cheaper?
Not ready to book yet? You can track prices for flights from Singapore to Midway on Cheapflights with our Price Alert feature and get notified when better prices are available.