Cheap flights from North America to Chicago from $65

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from North America to Chicago departing on 9/14. 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
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.

Find the cheapest flights from North America to Chicago

Cheap round-trip flights

Frontier Logo
8:00 am - 10:40 amDFW-ORD
2h 40mnonstop
Frontier Logo
6:00 am - 9:16 amORD-DFW
27h 16m1 stop
$114Frontier
Find Deal
Wed, Sep 17 - Sun, Sep 21
Frontier Logo
8:00 am - 1:38 pmDFW-MDW
5h 38m1 stop
Frontier Logo
5:20 pm - 8:01 pmMDW-DFW
2h 41mnonstop
$114Frontier
Find Deal
Wed, Oct 8 - Tue, Oct 14
Spirit Airlines Logo
7:20 am - 9:44 amDFW-ORD
2h 24mnonstop
Spirit Airlines Logo
3:11 pm - 5:42 pmORD-DFW
2h 31mnonstop
$121Spirit Airlines
Find Deal
Tue, Dec 9 - Fri, Dec 12
Spirit Airlines Logo
6:47 pm - 9:15 pmDFW-ORD
2h 28mnonstop
Spirit Airlines Logo
3:11 pm - 5:42 pmORD-DFW
2h 31mnonstop
$128Spirit Airlines
Find Deal
Mon, Dec 8 - Thu, Dec 11
American Airlines Logo
5:33 pm - 8:01 pmDFW-ORD
2h 28mnonstop
American Airlines Logo
4:12 pm - 6:45 pmORD-DFW
2h 33mnonstop
$157American Airlines
Find Deal
Wed, Sep 24 - Tue, Sep 30
United Airlines Logo
9:18 am - 10:55 amLGA-ORD
2h 37mnonstop
United Airlines Logo
11:00 am - 2:19 pmORD-LGA
2h 19mnonstop
$157United Airlines
Find Deal
Sat, Sep 13 - Wed, Sep 17
United Airlines Logo
9:30 pm - 11:07 pmLGA-ORD
2h 37mnonstop
United Airlines Logo
6:00 am - 9:16 amORD-LGA
2h 16mnonstop
$169United Airlines
Find Deal
Fri, Sep 19 - Sun, Sep 21
American Airlines Logo
7:48 pm - 9:21 pmLGA-ORD
2h 33mnonstop
American Airlines Logo
6:00 am - 9:00 amORD-LGA
2h 00mnonstop
$173American Airlines
Find Deal
Sat, Sep 13 - Mon, Sep 15
Southwest Logo
10:30 am - 10:00 pmSEA-ORD
9h 30m1 stop
Southwest Logo
4:20 pm - 10:30 pmORD-SEA
8h 10m1 stop
$203Southwest
Find Deal
Sat, Aug 30 - Sat, Sep 6
Southwest Logo
5:15 am - 2:10 pmSEA-ORD
6h 55m1 stop
Southwest Logo
7:30 am - 1:40 pmORD-SEA
8h 10m1 stop
$208Southwest
Find Deal
Tue, Sep 16 - Tue, Sep 23

JetBlue flights from North America to Chicago

Our best JetBlue deals on North America to Chicago flight tickets
JetBlue
Sep 4
JFK10:30 amNew York John F Kennedy Intl
2h 40m
ORD12:10 pmChicago O'Hare Intl
Sep 8
ORD6:45 amChicago O'Hare Intl
2h 14m
JFK9:59 amNew York John F Kennedy Intl
JetBlue
Sep 13
JFK2:30 pmNew York John F Kennedy Intl
2h 51m
ORD4:21 pmChicago O'Hare Intl
Sep 16
ORD6:45 amChicago O'Hare Intl
2h 14m
JFK9:59 amNew York John F Kennedy Intl
JetBlue
Sep 4
JFK10:30 amNew York John F Kennedy Intl
2h 40m
ORD12:10 pmChicago O'Hare Intl
Sep 8
ORD6:45 amChicago O'Hare Intl
2h 14m
JFK9:59 amNew York John F Kennedy Intl

American Airlines flights from North America to Chicago

Our best American Airlines deals on North America to Chicago flight tickets
American Airlines
Sep 24
DFW5:33 pmDallas/Fort Worth
2h 28m
ORD8:01 pmChicago O'Hare Intl
Sep 30
ORD4:12 pmChicago O'Hare Intl
2h 33m
DFW6:45 pmDallas/Fort Worth
American Airlines
Sep 13
LGA7:48 pmNew York LaGuardia
2h 33m
ORD9:21 pmChicago O'Hare Intl
Sep 15
ORD6:00 amChicago O'Hare Intl
2h 00m
LGA9:00 amNew York LaGuardia
American Airlines
Oct 27
EWR7:40 pmNewark
2h 44m
ORD9:24 pmChicago O'Hare Intl
Oct 28
ORD8:35 pmChicago O'Hare Intl
2h 24m
EWR11:59 pmNewark

momondo Fare Finder

 
Customize your flight search to find flights from North America 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 August 18, 2025.
Use the filters below to find and compare flights from North America to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Wed 9/17

8:00 am-10:40 am

Nonstop2h 40m

Chicago O'Hare Intl

Sun 9/21

6:00 am-9:16 am

1 stop27h 16m

$114

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Wed 10/8

8:00 am-1:38 pm

1 stop5h 38m

Chicago Midway

Tue 10/14

5:20 pm-8:01 pm

Nonstop2h 41m

$114

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Tue 12/9

7:20 am-9:44 am

Nonstop2h 24m

Chicago O'Hare Intl

Fri 12/12

3:11 pm-5:42 pm

Nonstop2h 31m

$121

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Mon 12/8

6:47 pm-9:15 pm

Nonstop2h 28m

Chicago O'Hare Intl

Thu 12/11

3:11 pm-5:42 pm

Nonstop2h 31m

$128

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Wed 9/24

5:33 pm-8:01 pm

Nonstop2h 28m

Chicago O'Hare Intl

Tue 9/30

4:12 pm-6:45 pm

Nonstop2h 33m

$157

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 9/13

9:18 am-10:55 am

Nonstop2h 37m

Chicago O'Hare Intl

Wed 9/17

11:00 am-2:19 pm

Nonstop2h 19m

$157

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 9/19

9:30 pm-11:07 pm

Nonstop2h 37m

Chicago O'Hare Intl

Sun 9/21

6:00 am-9:16 am

Nonstop2h 16m

$169

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 9/13

7:48 pm-9:21 pm

Nonstop2h 33m

Chicago O'Hare Intl

Mon 9/15

6:00 am-9:00 am

Nonstop2h 00m

$173

SeattleChicago

SEA - ORD

SEAORD

Seattle/Tacoma Intl

Sat 8/30

10:30 am-10:00 pm

1 stop9h 30m

Chicago O'Hare Intl

Sat 9/6

4:20 pm-10:30 pm

1 stop8h 10m

$203

SeattleChicago

SEA - ORD

SEAORD

Seattle/Tacoma Intl

Tue 9/16

5:15 am-2:10 pm

1 stop6h 55m

Chicago O'Hare Intl

Tue 9/23

7:30 am-1:40 pm

1 stop8h 10m

$208

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Chicago from

How to get the cheapest flight ticket from North America 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

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from North America, with most prices found around $180. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from North America to Chicago during January average around $181.

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

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $293. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from North America to Chicago for around $383.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from North America to Chicago during this time can be as low as $251. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $354.

What is the cheapest North America to Chicago flight route?

Fly from Newark to Chicago Midway for the best North America - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from North America when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $249 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from North America for as low as $197 on momondo.

What cabin class options are available on North America to Chicago flights?

There are 4 cabin classes available to choose from on North America to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on North America to Chicago flights?

No. A direct flight is the cheapest option for a flight between North America to Chicago.

Cheap North America to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from North America to Chicago

Best Price Found

$65

Fastest flight time

2h 03m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from North America in the past 72 hours is $65. The best round-trip flight deal from North America to Chicago found on momondo in the last 72 hours is $114.
The fastest flight from North America to Chicago takes 2h 03m
Direct flights go from North America to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
  • When did momondo last update prices for flights from North America to Chicago?

    Prices for flights from North America to Chicago were last updated today.

  • How many operators does momondo search for flights from North America to Chicago?

  • How old do you have to be to fly from North America 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 North America to Chicago.

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

    The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from North America to Chicago?

Best airlines flying from North America to Chicago

Compare and see reviews for airlines that fly from North America to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $35Free CancellationRating
6.3
8,038 reviews
Search Spirit Airlines flights
FrontierPriceFrom $56Free CancellationRating
5.8
3,212 reviews
Search Frontier flights
JetBluePriceFrom $76Free CancellationRating
7.2
2,915 reviews
Search JetBlue flights
United AirlinesPriceFrom $97Free CancellationRating
7.4
8,925 reviews
Search United Airlines flights
DeltaPriceFrom $98Free CancellationRating
8.0
7,981 reviews
Search Delta flights
Allegiant AirPriceFrom $100Free CancellationRating
7.2
701 reviews
Search Allegiant Air flights
Hawaiian AirlinesPriceFrom $108Free CancellationRating
7.8
2,665 reviews
Search Hawaiian Airlines flights
SouthwestPriceFrom $126Free CancellationRating
8.0
4,246 reviews
Search Southwest flights
Sun Country AirPriceFrom $130Free CancellationRating
6.9
333 reviews
Search Sun Country Air flights
American AirlinesPriceFrom $137Free CancellationRating
7.2
10,000 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
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from North America.

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

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

How can momondo help me find flights from North America to Chicago?

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

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

Price alerts on flights to Chicago from North America 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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 8/23
Sat 8/30

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