Cheap flights from St. John's, Saint John to Chicago from $390

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from St. John's, Saint John to Chicago departing on 4/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Find the cheapest flights from St. John's, Saint John to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
1:52 pm - 7:44 am
ANU
-
ORD
18h 52m
1 stop
Multiple Airlines Logo
3:50 pm - 2:10 pm
ORD
-
ANU
21h 20m
1 stop
$600Multiple Airlines
Sat, May 9 - Sat, May 16
JetBlue Logo
1:52 pm - 7:44 am
ANU
-
ORD
18h 52m
1 stop
JetBlue Logo
7:20 am - 12:33 pm
ORD
-
ANU
28h 13m
2 stops
$641JetBlue
Sat, May 9 - Sat, May 16
JetBlue Logo
1:52 pm - 7:44 am
ANU
-
ORD
18h 52m
1 stop
JetBlue Logo
8:35 am - 12:47 pm
ORD
-
ANU
27h 12m
1 stop
$687JetBlue
Fri, May 8 - Fri, May 15
JetBlue Logo
1:52 pm - 8:53 pm
ANU
-
ORD
32h 01m
2 stops
JetBlue Logo
7:20 am - 12:33 pm
ORD
-
ANU
28h 13m
2 stops
$767JetBlue
Sat, May 9 - Sat, May 16
Multiple Airlines Logo
5:45 pm - 6:50 pm
ANU
-
ORD
26h 05m
2 stops
Multiple Airlines Logo
7:45 pm - 6:55 pm
ORD
-
ANU
22h 10m
2 stops
$837Multiple Airlines
Fri, May 8 - Fri, May 15
Multiple Airlines Logo
5:45 pm - 6:50 pm
ANU
-
ORD
26h 05m
2 stops
Multiple Airlines Logo
11:51 am - 6:55 pm
ORD
-
ANU
30h 04m
3 stops
$873Multiple Airlines
Fri, May 8 - Fri, May 15
American Airlines Logo
1:15 pm - 11:54 pm
ANU
-
ORD
11h 39m
2 stops
American Airlines Logo
8:46 pm - 2:25 pm
ORD
-
ANU
16h 39m
1 stop
$897American Airlines
Fri, May 8 - Fri, May 15
Multiple Airlines Logo
8:30 am - 2:05 pm
ANU
-
ORD
30h 35m
3 stops
Multiple Airlines Logo
11:51 am - 6:55 pm
ORD
-
ANU
30h 04m
3 stops
$938Multiple Airlines
Fri, May 8 - Fri, May 15
Multiple Airlines Logo
5:45 pm - 11:15 pm
ANU
-
ORD
30h 30m
3 stops
Multiple Airlines Logo
12:53 pm - 2:10 pm
ORD
-
ANU
24h 17m
2 stops
$1,011Multiple Airlines
Sat, May 9 - Sat, May 16
Multiple Airlines Logo
5:45 pm - 11:15 pm
ANU
-
ORD
30h 30m
3 stops
Multiple Airlines Logo
10:31 am - 2:10 pm
ORD
-
ANU
26h 39m
3 stops
$1,135Multiple Airlines
Sat, May 9 - Sat, May 16

JetBlue flights from St. John's, Saint John to Chicago

Our best JetBlue deals on St. John's, Saint John to Chicago flight tickets
JetBlue
May 9
ANU1:52 pmSt. John's V.C. Bird Intl
18h 52m
1 stop
ORD7:44 amChicago O'Hare Intl
May 16
ORD7:20 amChicago O'Hare Intl
28h 13m
2 stops
ANU12:33 pmSt. John's V.C. Bird Intl
$641
JetBlue
May 8
ANU1:52 pmSt. John's V.C. Bird Intl
18h 52m
1 stop
ORD7:44 amChicago O'Hare Intl
May 15
ORD8:35 amChicago O'Hare Intl
27h 12m
1 stop
ANU12:47 pmSt. John's V.C. Bird Intl
$687
JetBlue
May 9
ANU1:52 pmSt. John's V.C. Bird Intl
32h 01m
2 stops
ORD8:53 pmChicago O'Hare Intl
May 16
ORD7:20 amChicago O'Hare Intl
28h 13m
2 stops
ANU12:33 pmSt. John's V.C. Bird Intl
$767

momondo Fare Finder

 
Customize your flight search to find flights from St. John's, Saint John to Chicago 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 March 26, 2026.
Use the filters below to find and compare flights from St. John's, Saint John to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

St. John'sChicago

ANU - ORD

ANUORD

St. John's V.C. Bird Intl

Sat 5/9

1:52 pm-7:44 am

1 stop18h 52m

Chicago O'Hare Intl

Sat 5/16

3:50 pm-2:10 pm

1 stop21h 20m

$600

St. John'sChicago

ANU - ORD

ANUORD

St. John's V.C. Bird Intl

Sat 5/9

1:52 pm-7:44 am

1 stop18h 52m

Chicago O'Hare Intl

Sat 5/16

7:20 am-12:33 pm

2 stops28h 13m

$641

St. John'sChicago

ANU - ORD

ANUORD

St. John's V.C. Bird Intl

Fri 5/8

1:52 pm-7:44 am

1 stop18h 52m

Chicago O'Hare Intl

Fri 5/15

8:35 am-12:47 pm

1 stop27h 12m

$687

St. John'sChicago

ANU - ORD

ANUORD

St. John's V.C. Bird Intl

Sat 5/9

1:52 pm-8:53 pm

2 stops32h 01m

Chicago O'Hare Intl

Sat 5/16

7:20 am-12:33 pm

2 stops28h 13m

$767

St. John'sChicago

ANU - ORD

ANUORD

St. John's V.C. Bird Intl

Fri 5/8

5:45 pm-6:50 pm

2 stops26h 05m

Chicago O'Hare Intl

Fri 5/15

7:45 pm-6:55 pm

2 stops22h 10m

$837

St. John'sChicago

ANU - ORD

ANUORD

St. John's V.C. Bird Intl

Fri 5/8

5:45 pm-6:50 pm

2 stops26h 05m

Chicago O'Hare Intl

Fri 5/15

11:51 am-6:55 pm

3 stops30h 04m

$873
Quickest round-trip

St. John'sChicago

ANU - ORD

ANUORD

St. John's V.C. Bird Intl

Fri 5/8

1:15 pm-11:54 pm

2 stops11h 39m

Chicago O'Hare Intl

Fri 5/15

8:46 pm-2:25 pm

1 stop16h 39m

$897

St. John'sChicago

ANU - ORD

ANUORD

St. John's V.C. Bird Intl

Fri 5/8

8:30 am-2:05 pm

3 stops30h 35m

Chicago O'Hare Intl

Fri 5/15

11:51 am-6:55 pm

3 stops30h 04m

$938

St. John'sChicago

ANU - ORD

ANUORD

St. John's V.C. Bird Intl

Sat 5/9

5:45 pm-11:15 pm

3 stops30h 30m

Chicago O'Hare Intl

Sat 5/16

12:53 pm-2:10 pm

2 stops24h 17m

$1,011

St. John'sChicago

ANU - ORD

ANUORD

St. John's V.C. Bird Intl

Sat 5/9

5:45 pm-11:15 pm

3 stops30h 30m

Chicago O'Hare Intl

Sat 5/16

10:31 am-2:10 pm

3 stops26h 39m

$1,135

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from St. John's, Saint John to Chicago

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

Can stopping save me money on St. John's, Saint John to Chicago flights?

You could potentially save up to 56% on your flight if you consider stops on a St. John's, Saint John to Chicago flight.

When to book flights from St. John's, Saint John to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from St. John's, Saint John to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap St. John's, Saint John to Chicago (ANU to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from St. John's, Saint John to Chicago

Fastest flight time

18h 52m

Direct flights

None
The fastest flight from St. John's, Saint John to Chicago takes 18h 52m
There are no direct flights from St. John's, Saint John to Chicago. There are no popular flight routes from St. John's, Saint John to Chicago.
  • How far is St. John's V.C. Bird Intl to Chicago by plane?

    The distance between St. John's V.C. Bird Intl and Chicago is about 2288.8 mi. A reasonable flight in good conditions will take 18h 52m.

  • When did momondo last update prices for flights from St. John's V.C. Bird Intl Airport to Chicago?

    Prices for flights from St. John's V.C. Bird Intl Airport to Chicago were last updated today.

  • How many operators does momondo search for flights from St. John's V.C. Bird Intl Airport to Chicago?

  • How old do you have to be to fly from St. John's V.C. Bird Intl Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from St. John's V.C. Bird Intl Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents you'll need for your trip to Chicago 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 Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Best airlines flying from St. John's, Saint John to Chicago

Compare and see reviews for airlines that fly from St. John's, Saint John to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $552Free CancellationRating
7.1
11,495 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

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Can I find flights from St. John's to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for St. John's to Chicago flights to just show those with flexible booking policies.

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Once you have performed a search for St. John's to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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1 adult
Sat 4/25
Sat 5/2

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago