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S$ 101+ 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 7-7. 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 Jun — 3 Jul1
1 adult
1 adult, Economy, 0 bags

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 27 May 2026. In the last 7 days, Cheapflights users made a total of 200,618 searches

Fly to

Route

Depart

Return

Price

Cheapest return flight
Fastest return journey

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Wed 8-7

13:55-16:00

Nonstop1h 05m

Grand Rapids Gerald R. Ford Intl

Wed 15-7

14:06-14:15

Nonstop1h 09m

S$ 226

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Tue 20-10

21:50-23:54

Nonstop1h 04m

Grand Rapids Gerald R. Ford Intl

Tue 27-10

06:00-06:10

Nonstop1h 10m

S$ 226

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Tue 7-7

17:18-23:55

1 stop5h 37m

Grand Rapids Gerald R. Ford Intl

Wed 8-7

05:30-07:59

1 stop3h 29m

S$ 291

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Fri 21-8

06:51-13:53

1 stop6h 02m

Grand Rapids Gerald R. Ford Intl

Sat 5-9

12:03-16:17

1 stop5h 14m

S$ 326

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Sun 6-9

06:51-11:20

1 stop3h 29m

Grand Rapids Gerald R. Ford Intl

Tue 15-9

05:30-08:02

1 stop3h 32m

S$ 327

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Thu 9-7

17:18-23:55

1 stop5h 37m

Grand Rapids Gerald R. Ford Intl

Thu 16-7

05:30-07:59

1 stop3h 29m

S$ 362

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Mon 3-8

19:25-23:55

1 stop3h 30m

Grand Rapids Gerald R. Ford Intl

Mon 10-8

05:30-07:56

1 stop3h 26m

S$ 362

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Sat 4-7

18:02-20:12

Nonstop1h 10m

Grand Rapids Gerald R. Ford Intl

Tue 7-7

06:00-06:18

Nonstop1h 18m

S$ 370

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Mon 6-7

13:40-21:00

1 stop6h 20m

Grand Rapids Gerald R. Ford Intl

Thu 9-7

08:15-13:03

1 stop5h 48m

S$ 395

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 5-9

13:50-00:59

2 stops10h 09m

Portland

Sun 6-9

06:30-10:23

1 stop4h 53m

S$ 399

Flights are sorted by cheapest return flights first.

Deals found on 26-5

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.

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

Currently, January is the cheapest month in which you can book a flight from Chicago (average of S$ 628). Flying from Chicago in December will prove the most costly (average of S$ 1,244). 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$ 2,812
United Airlines
United Airlines
From S$ 1,819

What are popular destinations to fly to from Chicago?

From Chicago you can expect to find greater availability for the following destinations: Detroit (1,334 flights per day), New York (1,094 flights per day) and Los Angeles (788 flights per day).

Las Vegas Harry Reid Intl
Las Vegas Harry Reid Intl
From S$ 53
Amman Queen Alia Intl
Amman Queen Alia Intl
From S$ 913
Detroit
Detroit
From S$ 1,678

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
Jacksonville
Jacksonville
From S$ 190

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

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 43 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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 Etihad Airways from Chicago. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Etihad Airways
7.3
Good
1,445 reviews
Check prices

Food

7.2

Overall

7.3

Crew

7.8

Entertainment

7.2

Boarding

7.6

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Tom,May 2026

JFK - AUH

Everything was good except the lie flat bed. The bed has a gap and is uncomfortable to lie on. The hostesses were great; the food service was reasonable and the connecting flight services and the baggage service were good. Entertainment service was also good.
Etihad Airways
7.3
Good
1,445 reviews
Etihad Airways
7.3
Good
1,445 reviews
Check prices

Food

7.2

Overall

7.3

Crew

7.8

Entertainment

7.2

Boarding

7.6

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Tom,May 2026

JFK - AUH

Everything was good except the lie flat bed. The bed has a gap and is uncomfortable to lie on. The hostesses were great; the food service was reasonable and the connecting flight services and the baggage service were good. Entertainment service was also good.

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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 27 May 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 27 May 2026.

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

    This month, the top selected destinations from Chicago are Atlanta, Boston, Athens. Throughout the year, Boston, Atlanta, 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 January. 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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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

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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