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S$ 142+ Cheap flights from Chicago

This is the cheapest return flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1-3. 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
26 Jan — 2 Feb1
1 adult

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 21 January 2025.

Good round-trip deal

S$ 270 or less

Good one-way deal

S$ 83 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

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 21 January 2025.

Sat 31-506:20ORD - PWM
1 stop6h 00mJetBlue
Sat 7-614:15PWM - ORD
1 stop9h 05mJetBlue
Deal found 20-1S$ 251
Sun 9-211:10ORD - PWM
Nonstop2h 32mUnited Airlines
Sun 16-216:53PWM - ORD
Nonstop3h 02mUnited Airlines
Deal found 19-1S$ 283
Mon 17-207:05ORD - PWM
1 stop6h 17mDelta
Thu 20-206:00PWM - ORD
1 stop5h 49mDelta
Deal found 21-1S$ 290
Wed 5-307:00ORD - PWM
1 stop4h 30mSouthwest
Tue 11-306:00PWM - ORD
1 stop8h 05mSouthwest
Deal found 20-1S$ 294
Wed 19-205:45ORD - ONT
1 stop9h 10mSouthwest
Wed 26-212:25ONT - ORD
2 stops8h 10mSouthwest
Deal found 20-1S$ 342
Sat 8-317:13ORD - ONT
1 stop7h 39mDelta
Wed 12-311:42ONT - ORD
1 stop10h 11mDelta
Deal found 21-1S$ 349
Fri 18-415:16ORD - ONT
1 stop10h 43mAlaska Airlines
Tue 22-411:46ONT - ORD
1 stop10h 13mAlaska Airlines
Deal found 20-1S$ 362
Fri 28-314:00ORD - GRR
Nonstop1h 06mUnited Airlines
Sun 30-309:20GRR - ORD
Nonstop1h 05mUnited Airlines
Deal found 20-1S$ 373
Fri 14-218:15ORD - GRR
1 stop3h 42mDelta
Sat 15-217:57GRR - ORD
1 stop4h 17mDelta
Deal found 21-1S$ 377
Sat 21-606:30ORD - ONT
1 stop8h 04mUnited Airlines
Sat 28-613:00ONT - ORD
1 stop7h 25mUnited Airlines
Deal found 21-1S$ 402
Sun 6-720:10ORD - PWM
1 stop14h 25mSun Country Air
Fri 11-712:32PWM - ORD
1 stop7h 39mSun Country Air
Deal found 20-1S$ 434
Sun 2-219:05ORD - ATH
1 stop21h 30mSWISS
Tue 11-217:40ATH - ORD
1 stop30h 35mSWISS
Deal found 20-1S$ 745

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 21 January 2025. In the last 7 days, Cheapflights users made a total of 200,618 searches

Fly to

Any airport

Route

Depart

Return

Price

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 31-5

06:20-13:20

1 stop6h 00m

Portland

Sat 7-6

14:15-22:20

1 stop9h 05m

S$ 251

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sun 9-2

11:10-14:42

Nonstop2h 32m

Portland

Sun 16-2

16:53-18:55

Nonstop3h 02m

S$ 283

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Mon 17-2

07:05-14:22

1 stop6h 17m

Portland

Thu 20-2

06:00-10:49

1 stop5h 49m

S$ 290

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 5-3

07:00-12:30

1 stop4h 30m

Portland

Tue 11-3

06:00-13:05

1 stop8h 05m

S$ 294

ChicagoOntario

ORD - ONT

ORDONT

Chicago O'Hare Intl

Wed 19-2

05:45-12:55

1 stop9h 10m

Ontario

Wed 26-2

12:25-22:35

2 stops8h 10m

S$ 342

ChicagoOntario

ORD - ONT

ORDONT

Chicago O'Hare Intl

Sat 8-3

17:13-22:52

1 stop7h 39m

Ontario

Wed 12-3

11:42-23:53

1 stop10h 11m

S$ 349

ChicagoOntario

ORD - ONT

ORDONT

Chicago O'Hare Intl

Fri 18-4

15:16-23:59

1 stop10h 43m

Ontario

Tue 22-4

11:46-23:59

1 stop10h 13m

S$ 362

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Fri 28-3

14:00-16:06

Nonstop1h 06m

Grand Rapids Gerald R. Ford Intl

Sun 30-3

09:20-09:25

Nonstop1h 05m

S$ 373

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Fri 14-2

18:15-22:57

1 stop3h 42m

Grand Rapids Gerald R. Ford Intl

Sat 15-2

17:57-21:14

1 stop4h 17m

S$ 377

ChicagoOntario

ORD - ONT

ORDONT

Chicago O'Hare Intl

Sat 21-6

06:30-12:34

1 stop8h 04m

Ontario

Sat 28-6

13:00-22:25

1 stop7h 25m

S$ 402

Flights are sorted by cheapest return flights first.

Deals found on 21-1

Showing 1-10 of 60 results
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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 17 January 2025.

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 50 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, February is the cheapest month in which you can book a flight from Chicago (average of S$ 1,009). Flying from Chicago in June will prove the most costly (average of S$ 1,693). 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: United Airlines. As it departs for the following popular destinations: Singapore.

United Airlines

United Airlines

From S$ 836

What are popular destinations to fly to from Chicago?

From Chicago you can expect to find greater availability for the following destinations: New York (1,543 flights per day), Detroit (990 flights per day) and Orlando (815 flights per day).

San Francisco

San Francisco

From S$ 107

Rome

Rome

From S$ 719

Atlanta Hartsfield-Jackson

Atlanta Hartsfield-Jackson

From S$ 2,310

Buffalo

Buffalo

From S$ 199

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Orlando, with prices starting at S$ 83. Explore other affordable destinations below.

Orlando

Orlando

From S$ 61

San Francisco

San Francisco

From S$ 107

Buffalo

Buffalo

From S$ 199

Rome

Rome

From S$ 719

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.
Korean Air
8.5
Very Good
1,039 reviews
Check prices

Comfort

8.3

Crew

8.7

Overall

8.5

Boarding

8.5

Entertainment

8.2

Food

8.1

Reviews

1 / 10

Flight was short, so we did not get food, but that is expected. Only have entertainment a fair rating because no wifi is provided onboard. Good flight overall.

Korean Air
8.5
Very Good
1,039 reviews
Korean Air
8.5
Very Good
1,039 reviews
Check prices

Comfort

8.3

Crew

8.7

Overall

8.5

Boarding

8.5

Entertainment

8.2

Food

8.1

Reviews

1 / 10

Flight was short, so we did not get food, but that is expected. Only have entertainment a fair rating because no wifi is provided onboard. Good flight overall.

EVA Air
8.4
Very Good
1,253 reviews
Korean Air
8.5
Very Good
1,039 reviews
Check prices

Comfort

8.3

Crew

8.7

Overall

8.5

Boarding

8.5

Entertainment

8.2

Food

8.1

Reviews

1 / 10

Flight was short, so we did not get food, but that is expected. Only have entertainment a fair rating because no wifi is provided onboard. Good flight overall.

Japan Airlines
8.3
Very Good
1,449 reviews
Korean Air
8.5
Very Good
1,039 reviews
Check prices

Comfort

8.3

Crew

8.7

Overall

8.5

Boarding

8.5

Entertainment

8.2

Food

8.1

Reviews

1 / 10

Flight was short, so we did not get food, but that is expected. Only have entertainment a fair rating because no wifi is provided onboard. Good flight overall.

Emirates
8.1
Very Good
3,358 reviews
Korean Air
8.5
Very Good
1,039 reviews
Check prices

Comfort

8.3

Crew

8.7

Overall

8.5

Boarding

8.5

Entertainment

8.2

Food

8.1

Reviews

1 / 10

Flight was short, so we did not get food, but that is expected. Only have entertainment a fair rating because no wifi is provided onboard. Good flight overall.

Singapore Airlines
8.1
Very Good
1,328 reviews
Korean Air
8.5
Very Good
1,039 reviews
Check prices

Comfort

8.3

Crew

8.7

Overall

8.5

Boarding

8.5

Entertainment

8.2

Food

8.1

Reviews

1 / 10

Flight was short, so we did not get food, but that is expected. Only have entertainment a fair rating because no wifi is provided onboard. Good flight overall.

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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 21 January 2025.

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

    This month, the top selected destinations from Chicago are Ahmedabad, Mumbai, Atlanta. Throughout the year, Atlanta, Boston, Athens 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 February. The most expensive month for flights is June. The cheapest prices are shown above but prices will vary according to departure times, airlines, class and how early you book.

  • Where are the cheapest places to fly to from Chicago?

    View the cheapest flight destinations from Chicago:
    Fly from Chicago to Singapore from S$ 979 round trip

  • 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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