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S$ 90+ Cheap flights from Chicago

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 7-4. 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.
CHI — SIN
1 Apr — 8 Apr1
1 adult
1 adult, Economy, 0 bags

What to know about flights from Chicago

Discover essential information about flights departing from Chicago, including flight schedules, destinations, airlines operating at the Chicago airport, and any specific guidelines or requirements for travellers. Please note that the information is based on the most recent updates available. Data last updated 2 March 2026.

Good round-trip deal

S$ 188 or less

Good one-way deal

S$ 55 or less
Price to beat on a round-trip flight from Chicago.
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Price to beat on a one-way flight from Chicago.
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Find flights from Chicago

Enter your travel dates to find the best prices.

Cheapest flights from Chicago
Explore the most affordable flight options available from Chicago. Find the lowest fares based on data from user searches, with prices last updated on 2 March 2026.

Thu 2-413:55
ORD
-
GRR
Nonstop1h 05m
United Airlines
Thu 30-421:20
GRR
-
ORD
Nonstop1h 01m
United Airlines
Deal found 28-2S$ 216
Wed 20-517:07
ORD
-
GRR
Nonstop1h 06m
United Airlines
Sat 23-513:51
GRR
-
ORD
Nonstop1h 12m
United Airlines
Deal found 26-2S$ 243
Tue 24-321:46
ORD
-
GRR
Nonstop1h 07m
United Airlines
Thu 26-312:55
GRR
-
ORD
Nonstop1h 13m
United Airlines
Deal found 27-2S$ 252
Fri 3-418:10
ORD
-
PWM
Nonstop2h 30m
United Airlines
Sun 5-418:33
PWM
-
ORD
Nonstop3h 10m
United Airlines
Deal found 27-2S$ 264
Wed 20-507:00
ORD
-
GRR
1 stop3h 18m
Delta
Sat 23-505:30
GRR
-
ORD
1 stop3h 57m
Delta
Deal found 26-2S$ 268
Sat 4-407:10
ORD
-
PWM
1 stop3h 59m
Delta
Tue 7-414:30
PWM
-
ORD
1 stop8h 19m
Delta
Deal found 26-2S$ 269
Mon 23-319:53
ORD
-
GRR
Nonstop1h 06m
United Airlines
Thu 26-306:07
GRR
-
ORD
Nonstop1h 13m
United Airlines
Deal found 27-2S$ 272
Tue 19-514:00
ORD
-
PWM
2 stops9h 43m
Delta
Fri 22-514:05
PWM
-
ORD
1 stop8h 48m
Delta
Deal found 26-2S$ 276
Fri 10-418:10
ORD
-
PWM
Nonstop2h 30m
United Airlines
Mon 13-419:36
PWM
-
ORD
1 stop5h 07m
United Airlines
Deal found 26-2S$ 277
Sun 10-506:00
ORD
-
PWM
1 stop6h 10m
Delta
Fri 15-512:55
PWM
-
ORD
1 stop6h 10m
Delta
Deal found 26-2S$ 278
Tue 19-508:45
ORD
-
PWM
1 stop5h 04m
United Airlines
Wed 27-505:15
PWM
-
ORD
1 stop5h 21m
United Airlines
Deal found 27-2S$ 289
Sat 9-518:31
ORD
-
PWM
1 stop5h 12m
Delta
Sat 16-514:05
PWM
-
ORD
1 stop8h 48m
Delta
Deal found 26-2S$ 294

Find flights from Chicago within your budget

 
Find flights departing from Chicago that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on 2 March 2026. In the last 7 days, Cheapflights users made a total of 200,618 searches

Fly to

Route

Depart

Return

Price

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Thu 2-4

13:55-16:00

Nonstop1h 05m

Grand Rapids Gerald R. Ford Intl

Thu 30-4

21:20-21:21

Nonstop1h 01m

S$ 216

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Wed 20-5

17:07-19:13

Nonstop1h 06m

Grand Rapids Gerald R. Ford Intl

Sat 23-5

13:51-14:03

Nonstop1h 12m

S$ 243

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Tue 24-3

21:46-23:53

Nonstop1h 07m

Grand Rapids Gerald R. Ford Intl

Thu 26-3

12:55-13:08

Nonstop1h 13m

S$ 252

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 21-4

18:10-21:40

Nonstop2h 30m

Portland

Sat 25-4

06:00-07:55

Nonstop2h 55m

S$ 264

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Wed 20-5

07:00-11:18

1 stop3h 18m

Grand Rapids Gerald R. Ford Intl

Sat 23-5

05:30-08:27

1 stop3h 57m

S$ 268

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 21-4

18:21-00:46

1 stop5h 25m

Portland

Sat 25-4

13:12-20:16

1 stop8h 04m

S$ 289

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 9-5

18:31-00:43

1 stop5h 12m

Portland

Sat 16-5

14:05-21:53

1 stop8h 48m

S$ 294

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Mon 30-3

17:40-23:42

1 stop5h 02m

Grand Rapids Gerald R. Ford Intl

Mon 6-4

14:21-16:43

1 stop3h 22m

S$ 320

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Sat 21-3

07:10-13:41

1 stop5h 31m

Grand Rapids Gerald R. Ford Intl

Mon 23-3

15:34-20:17

1 stop5h 43m

S$ 336

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Tue 30-6

19:58-22:09

Nonstop1h 11m

Grand Rapids Gerald R. Ford Intl

Sun 5-7

14:10-14:19

Nonstop1h 09m

S$ 340

Flights are sorted by cheapest return flights first.

Deals found on 1-3

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Chicago

Have a flexible travel schedule? Discover the best time to fly from Chicago with our price prediction graph.
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.

Travel insights for flights from Chicago

Get recent, data-driven insights about flights from Chicago including ideal travel times, pricing trends, and more.

When is the best time to book a flight from Chicago?

Use this chart to determine the optimal time to book a return flight from Chicago to Singapore. Price data was last updated on 27 February 2026.

The price you pay for your flight from Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 6 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chicago?

Currently, September is the cheapest month in which you can book a flight from Chicago (average of S$ 838). Flying from Chicago in December will prove the most costly (average of S$ 1,661). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

Which airlines fly from Chicago?

When flying from Chicago check dates and pricing for the following: JetBlue, United Airlines. As they depart for the following popular destinations: Singapore.

JetBlue
JetBlue
From S$ 2,783
United Airlines
United Airlines
From S$ 1,800

What are popular destinations to fly to from Chicago?

From Chicago you can expect to find greater availability for the following destinations: New York (1,279 flights per day), Detroit (826 flights per day) and Toronto (798 flights per day).

New York
New York
From S$ 68
Las Vegas Harry Reid Intl
Las Vegas Harry Reid Intl
From S$ 53
Amman Queen Alia Intl
Amman Queen Alia Intl
From S$ 903
Abu Dhabi Zayed Intl
Abu Dhabi Zayed Intl
From S$ 1,354

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Las Vegas Harry Reid Intl, with prices starting at S$ 53. Explore other affordable destinations below.

Las Vegas Harry Reid Intl
Las Vegas Harry Reid Intl
From S$ 53
Pittsburgh
Pittsburgh
From S$ 59
New York
New York
From S$ 68
Jacksonville
Jacksonville
From S$ 188

Airline reviews for flights from Chicago

Get insights into the airlines that provide service from Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing airline for your flight from Chicago. In the last 7 days, Cheapflights users made a total of 200,618 searches.
Read reviews from past customers who have flown United Airlines, Etihad Airways, andTurkish Airlines from Chicago. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,375 reviews
Check prices

Comfort

7.3

Crew

8.1

Food

6.6

Overall

7.4

Boarding

7.7

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,375 reviews
United Airlines
7.4
Good
9,375 reviews
Check prices

Comfort

7.3

Crew

8.1

Food

6.6

Overall

7.4

Boarding

7.7

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
Etihad Airways
7.3
Good
1,420 reviews
United Airlines
7.4
Good
9,375 reviews
Check prices

Comfort

7.3

Crew

8.1

Food

6.6

Overall

7.4

Boarding

7.7

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
Turkish Airlines
7.3
Good
4,241 reviews
United Airlines
7.4
Good
9,375 reviews
Check prices

Comfort

7.3

Crew

8.1

Food

6.6

Overall

7.4

Boarding

7.7

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

Browse thousands of different options on Cheapflights for your next trip

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Fly your favourite airline from Chicago

Browse through various options for flying your favourite airline from Chicago. Flight routes are based on user searches made on Cheapflights and were last updated on 2 March 2026.
United Airlines flights from Chicago to Singapore

Related info for your journey

Access useful and relevant information related to your journey from Chicago. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated 2 March 2026.

  • What are the most popular destinations to fly to from Chicago?

    This month, the top selected destinations from Chicago are Atlanta, Boston, Austin. Throughout the year, Atlanta, Boston, Ahmedabad are some of the top choices made by users flying from Chicago.

  • What is the cheapest month to fly from Chicago?

    Currently, the cheapest month for flights from Chicago is September. The most expensive month for flights is December. The cheapest prices are shown above but prices will vary according to departure times, airlines, class and how early you book.

  • How does Cheapflights help users find flights from Chicago?

    When you search for this flight from Chicago, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the best flight for you.

  • Why should you use Cheapflights to find cheap flight tickets from Chicago?

    By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights from Chicago.

  • Can Cheapflights find flights from Chicago with no change fees?

    Users can book flights with no change fees policies with our dedicated filters. Book flights from Chicago flexibly with Cheapflights today.

  • Can Cheapflights notify me if prices for flights from Chicago become cheaper?

    Of course! You can now track prices for flights from Chicago and get an alert from Cheapflights when they change. Click the bell icon next to the flight deals above and provide your email address to set up price alerts.

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How does Cheapflights help users find flights from Chicago?

When you search for this flight from Chicago, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the best flight for you.

Why should you use Cheapflights to find cheap flight tickets from Chicago?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights from Chicago.

Can Cheapflights find flights from Chicago with no change fees?

Users can book flights with no change fees policies with our dedicated filters. Book flights from Chicago flexibly with Cheapflights today.

Can Cheapflights notify me if prices for flights from Chicago become cheaper?

Of course! You can now track prices for flights from Chicago and get an alert from Cheapflights when they change. Click the bell icon next to the flight deals above and provide your email address to set up price alerts.

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