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Cheap flights from Chicago Midway Airport to Singapore from $421

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Singapore departing on 1/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago Midway Airport to Singapore

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
5:25 pm - 12:10 amMDW-SIN
40h 45m2 stops
Delta Logo
10:40 am - 12:35 pmSIN-MDW
38h 55m2 stops
$1,138Delta
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Mon, Mar 2 - Tue, Mar 10
Delta Logo
5:59 pm - 12:10 amMDW-SIN
40h 11m2 stops
Delta Logo
1:35 am - 9:46 pmSIN-MDW
34h 11m2 stops
$1,144Delta
Find Deal
Sun, Jan 18 - Wed, Jan 28
Delta Logo
6:00 am - 5:00 amMDW-SIN
33h 00m2 stops
Delta Logo
1:35 am - 8:46 pmSIN-MDW
33h 11m2 stops
$1,188Delta
Find Deal
Mon, Feb 9 - Sat, Mar 7
Delta Logo
5:25 pm - 12:10 amMDW-SIN
40h 45m2 stops
Delta Logo
1:35 am - 9:46 pmSIN-MDW
34h 11m2 stops
$1,189Delta
Find Deal
Sat, Jan 17 - Tue, Jan 27
Multiple Airlines Logo
8:15 am - 1:05 pmMDW-SIN
38h 50m2 stops
Multiple Airlines Logo
2:25 pm - 4:30 amSIN-MDW
28h 05m2 stops
$1,228Multiple Airlines
Find Deal
Mon, Feb 9 - Sun, Mar 8
Multiple Airlines Logo
6:10 pm - 12:35 pmMDW-SIN
29h 25m2 stops
Multiple Airlines Logo
1:45 pm - 5:40 amSIN-MDW
28h 55m2 stops
$1,247Multiple Airlines
Find Deal
Sat, Apr 11 - Mon, Apr 20
Korean Air Logo
9:20 am - 5:00 amMDW-SIN
30h 40m2 stops
Korean Air Logo
1:10 am - 12:30 pmSIN-MDW
24h 20m2 stops
$1,518Korean Air
Find Deal
Sun, Apr 12 - Tue, Apr 14
KLM Logo
5:29 pm - 4:15 pmMDW-SIN
32h 46m2 stops
KLM Logo
1:40 am - 4:34 pmSIN-MDW
28h 54m2 stops
$1,581KLM
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Mon, Dec 8 - Sun, Dec 14
KLM Logo
5:29 pm - 4:15 pmMDW-SIN
32h 46m2 stops
KLM Logo
1:40 am - 4:34 pmSIN-MDW
28h 54m2 stops
$1,582KLM
Find Deal
Mon, Dec 8 - Sun, Dec 14
Korean Air Logo
9:30 am - 5:00 amMDW-SIN
30h 30m2 stops
Korean Air Logo
1:10 am - 12:35 pmSIN-MDW
24h 25m2 stops
$1,789Korean Air
Find Deal
Sat, Apr 4 - Thu, Apr 9

Delta flights from Chicago Midway Airport to Singapore

Our best Delta deals on Chicago Midway Airport to Singapore flight tickets
Delta
Mar 2
MDW5:25 pmChicago Midway
40h 45m
2 stops
SIN12:10 amSingapore Changi
Mar 10
SIN10:40 amSingapore Changi
38h 55m
2 stops
MDW12:35 pmChicago Midway
$1,138
Find similar
Delta
Jan 18
MDW5:59 pmChicago Midway
40h 11m
2 stops
SIN12:10 amSingapore Changi
Jan 28
SIN1:35 amSingapore Changi
34h 11m
2 stops
MDW9:46 pmChicago Midway
$1,144
Find similar
Delta
Feb 9
MDW6:00 amChicago Midway
33h 00m
2 stops
SIN5:00 amSingapore Changi
Mar 7
SIN1:35 amSingapore Changi
33h 11m
2 stops
MDW8:46 pmChicago Midway
$1,188
Find similar

Korean Air flights from Chicago Midway Airport to Singapore

Our best Korean Air deals on Chicago Midway Airport to Singapore flight tickets
Korean Air
Apr 12
MDW9:20 amChicago Midway
30h 40m
2 stops
SIN5:00 amSingapore Changi
Apr 14
SIN1:10 amSingapore Changi
24h 20m
2 stops
MDW12:30 pmChicago Midway
$1,518
Find similar
Korean Air
Apr 4
MDW9:30 amChicago Midway
30h 30m
2 stops
SIN5:00 amSingapore Changi
Apr 9
SIN1:10 amSingapore Changi
24h 25m
2 stops
MDW12:35 pmChicago Midway
$1,789
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport 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, momondo users made 832,500 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

Fly to

Route

Depart

Return

Price

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Mon 3/2

5:25 pm-12:10 am

2 stops40h 45m

Singapore Changi

Tue 3/10

10:40 am-12:35 pm

2 stops38h 55m

$1,138

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sun 1/18

5:59 pm-12:10 am

2 stops40h 11m

Singapore Changi

Wed 1/28

1:35 am-9:46 pm

2 stops34h 11m

$1,144

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

Mon 2/9

8:15 am-1:05 pm

2 stops38h 50m

Singapore Changi

Sun 3/8

2:25 pm-4:30 am

2 stops28h 05m

$1,228

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

Sun 4/12

9:20 am-5:00 am

2 stops30h 40m

Singapore Changi

Tue 4/14

1:10 am-12:30 pm

2 stops24h 20m

$1,518

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Mon 12/8

5:29 pm-4:15 pm

2 stops32h 46m

Singapore Changi

Sun 12/14

1:40 am-4:34 pm

2 stops28h 54m

$1,581

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Mon 12/8

5:29 pm-4:15 pm

2 stops32h 46m

Singapore Changi

Sun 12/14

1:40 am-4:34 pm

2 stops28h 54m

$1,582

ChicagoSingapore

MDW - SIN

MDWSIN

Chicago Midway

Sat 4/4

9:30 am-5:00 am

2 stops30h 30m

Singapore Changi

Thu 4/9

1:10 am-12:35 pm

2 stops24h 25m

$1,789

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Singapore from

How to get the cheapest flight ticket from Chicago Midway Airport to Singapore

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Singapore?

The cheapest day to depart from Chicago Midway Airport to Singapore is on a Tuesday when prices can be found for as low as $1,166. The most expensive day to fly to Singapore is Friday, with ticket prices averaging around $1,365.

What is the cheapest time of day to depart on your flight to Singapore?

At noon is the cheapest time of day to fly from Chicago Midway Airport to Singapore when you can find flight prices for as low as $1,148. Flying to Singapore at noon is an ideal time because this is during off-peak travel hours. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $1,434 on average. Flights to Singapore from Chicago Midway Airport in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

When to book flights from Chicago Midway Airport to Singapore

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Singapore according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Singapore (MDW to SIN) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Singapore

Direct flights

None
There are no direct flights from Chicago Midway Airport to Singapore. There are no popular flight routes from Chicago Midway Airport to Singapore.
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  • How far is Chicago Midway to Singapore Changi by plane?

    A flight from Chicago Midway to Singapore Changi will travel around 9365.9 mi. By plane, this route typically takes 25h 20m.

  • When did momondo last update prices for flights from Chicago Midway Airport to Singapore Changi Airport?

    Prices for flights from Chicago Midway Airport to Singapore Changi Airport are updated daily.

  • How old do you have to be to fly from Chicago Midway Airport to Singapore Changi Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to Singapore Changi Airport.

  • What documentation or ID do you need to fly to Singapore Changi Airport?

    The travel and health documents you'll need for your trip to Singapore Changi Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Singapore Changi Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Singapore?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Singapore. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Chicago to Singapore with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Chicago to Singapore flights to just show those with flexible booking policies.

How can momondo help me find flights from Chicago to Singapore?

momondo provides multiple filters to help you find the best flight to Singapore from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Singapore right now. Can momondo alert me if prices change?

Price alerts on flights to Singapore from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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