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Cheap flights from Dallas to Chicago from $50

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Dallas to Chicago departing on 11/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Cheap round-trip flights

Frontier Logo
8:55 pm - 11:26 pmDFW-ORD
2h 31mnonstop
Frontier Logo
5:25 am - 7:58 amORD-DFW
2h 33mnonstop
$96Frontier
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Thu, Oct 16 - Sun, Oct 19
Frontier Logo
5:38 pm - 8:09 pmDFW-ORD
2h 31mnonstop
Frontier Logo
2:00 pm - 4:48 pmORD-DFW
2h 48mnonstop
$105Frontier
Find Deal
Sat, Nov 1 - Wed, Nov 5
Spirit Airlines Logo
9:28 pm - 11:50 pmDFW-ORD
2h 22mnonstop
Spirit Airlines Logo
10:05 pm - 12:34 amORD-DFW
2h 29mnonstop
$106Spirit Airlines
Find Deal
Mon, Oct 27 - Tue, Nov 11
Logo
9:28 pm - 11:50 pmDFW-ORD
2h 22mnonstop
Logo
2:00 pm - 4:48 pmORD-DFW
2h 48mnonstop
$111
Find Deal
Mon, Nov 3 - Wed, Nov 12
Spirit Airlines Logo
3:16 pm - 5:37 pmDFW-ORD
2h 21mnonstop
Spirit Airlines Logo
6:32 pm - 9:06 pmORD-DFW
2h 34mnonstop
$112Spirit Airlines
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Thu, Oct 9 - Sun, Oct 12
Logo
3:16 pm - 5:37 pmDFW-ORD
2h 21mnonstop
Logo
5:25 am - 7:58 amORD-DFW
2h 33mnonstop
$114
Find Deal
Thu, Oct 9 - Sun, Oct 12
Southwest Logo
7:05 pm - 9:30 pmDAL-ORD
2h 25mnonstop
Southwest Logo
1:30 pm - 3:50 pmORD-DAL
2h 20mnonstop
$135Southwest
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Wed, Sep 3 - Wed, Sep 10
Southwest Logo
2:20 pm - 4:35 pmDAL-MDW
2h 15mnonstop
Southwest Logo
5:30 pm - 7:45 pmMDW-DAL
2h 15mnonstop
$135Southwest
Find Deal
Thu, Sep 4 - Tue, Sep 9
Delta Logo
3:52 pm - 11:56 pmDAL-ORD
8h 04m1 stop
Delta Logo
5:45 am - 10:53 amORD-DAL
5h 08m1 stop
$197Delta
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Sat, Aug 30 - Wed, Sep 3
Delta Logo
3:52 pm - 9:26 pmDAL-MDW
5h 34m1 stop
Delta Logo
6:00 am - 10:54 amMDW-DAL
4h 54m1 stop
$197Delta
Find Deal
Tue, Sep 9 - Sat, Sep 13

Southwest flights from Dallas to Chicago

Our best Southwest deals on Dallas to Chicago flight tickets
Southwest
Sep 3
DAL7:05 pmDallas Love Field
2h 25m
ORD9:30 pmChicago O'Hare Intl
Sep 10
ORD1:30 pmChicago O'Hare Intl
2h 20m
DAL3:50 pmDallas Love Field
$135
Find similar
Southwest
Sep 2
DAL8:20 amDallas Love Field
2h 25m
ORD10:45 amChicago O'Hare Intl
Sep 9
ORD7:30 amChicago O'Hare Intl
2h 25m
DAL9:55 amDallas Love Field
$136
Find similar
Southwest
Oct 31
DAL6:40 amDallas Love Field
2h 10m
MDW8:50 amChicago Midway
Nov 3
MDW5:00 amChicago Midway
2h 30m
DAL7:30 amDallas Love Field
$142
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Frontier flights from Dallas to Chicago

Our best Frontier deals on Dallas to Chicago flight tickets
Frontier
Oct 16
DFW8:55 pmDallas/Fort Worth
2h 31m
ORD11:26 pmChicago O'Hare Intl
Oct 19
ORD5:25 amChicago O'Hare Intl
2h 33m
DFW7:58 amDallas/Fort Worth
$96
Find similar
Frontier
Nov 1
DFW5:38 pmDallas/Fort Worth
2h 31m
ORD8:09 pmChicago O'Hare Intl
Nov 5
ORD2:00 pmChicago O'Hare Intl
2h 48m
DFW4:48 pmDallas/Fort Worth
$105
Find similar
Frontier
Sep 23
DFW8:00 amDallas/Fort Worth
2h 40m
ORD10:40 amChicago O'Hare Intl
Sep 23
ORD6:44 pmChicago O'Hare Intl
2h 55m
DFW9:39 pmDallas/Fort Worth
$107
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momondo Fare Finder

 
Customize your flight search to find flights from Dallas 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 5, 2025.
Use the filters below to find and compare flights from Dallas to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Thu 10/16

8:55 pm-11:26 pm

Nonstop2h 31m

Chicago O'Hare Intl

Sun 10/19

5:25 am-7:58 am

Nonstop2h 33m

$96

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Sat 11/1

5:38 pm-8:09 pm

Nonstop2h 31m

Chicago O'Hare Intl

Wed 11/5

2:00 pm-4:48 pm

Nonstop2h 48m

$105

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Mon 10/27

9:28 pm-11:50 pm

Nonstop2h 22m

Chicago O'Hare Intl

Tue 11/11

10:05 pm-12:34 am

Nonstop2h 29m

$106

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Mon 11/3

9:28 pm-11:50 pm

Nonstop2h 22m

Chicago O'Hare Intl

Wed 11/12

2:00 pm-4:48 pm

Nonstop2h 48m

$111

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Thu 10/9

3:16 pm-5:37 pm

Nonstop2h 21m

Chicago O'Hare Intl

Sun 10/12

6:32 pm-9:06 pm

Nonstop2h 34m

$112

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Thu 10/9

3:16 pm-5:37 pm

Nonstop2h 21m

Chicago O'Hare Intl

Sun 10/12

5:25 am-7:58 am

Nonstop2h 33m

$114

DallasChicago

DAL - ORD

DALORD

Dallas Love Field

Wed 9/3

7:05 pm-9:30 pm

Nonstop2h 25m

Chicago O'Hare Intl

Wed 9/10

1:30 pm-3:50 pm

Nonstop2h 20m

$135

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Thu 9/4

2:20 pm-4:35 pm

Nonstop2h 15m

Chicago Midway

Tue 9/9

5:30 pm-7:45 pm

Nonstop2h 15m

$135

DallasChicago

DAL - ORD

DALORD

Dallas Love Field

Sat 8/30

3:52 pm-11:56 pm

1 stop8h 04m

Chicago O'Hare Intl

Wed 9/3

5:45 am-10:53 am

1 stop5h 08m

$197

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Tue 9/9

3:52 pm-9:26 pm

1 stop5h 34m

Chicago Midway

Sat 9/13

6:00 am-10:54 am

1 stop4h 54m

$197

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Dallas 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 Dallas, with most prices found around $133. If you’re not able to fly to Chicago in September, then February is your next best option. Flight prices from Dallas to Chicago during February average around $141.

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 Thursday when prices can be found for as low as $275. 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 Dallas to Chicago for around $894.

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 Dallas to Chicago during this time can be as low as $227. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $737.

What is the cheapest Dallas to Chicago flight route?

Fly from Dallas Love Field to Chicago Midway for the best Dallas - 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 Dallas when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $211 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Dallas for as low as $162 on momondo.

What cabin class options are available on Dallas to Chicago flights?

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

Cheap Dallas to Chicago flight deals and tips

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

Best Price Found

$50

Fastest flight time

2h 10m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Dallas in the past 72 hours is $50. The best round-trip flight deal from Dallas to Chicago found on momondo in the last 72 hours is $96.
The fastest flight from Dallas to Chicago takes 2h 10m
Direct flights go from Dallas to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
Search flight deals

  • How far is Dallas to Chicago by plane?

    A flight from Dallas to Chicago will travel around 804.0 mi. Typically, this will take 2h 10m by plane in normal conditions.

  • When did momondo last update prices for flights from Dallas to Chicago?

    Prices for flights from Dallas to Chicago refresh daily.

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

  • How old do you have to be to fly from Dallas to Chicago?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Dallas 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 Dallas to Chicago

Compare and see reviews for airlines that fly from Dallas to Chicago with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $55Free CancellationRating
5.8
3,232 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $57Free CancellationRating
6.3
8,052 reviews
Search Spirit Airlines flights
ContourPriceFrom $134Free CancellationRating
7.1
32 reviews
Search Contour flights
SouthwestPriceFrom $147Free CancellationRating
8.0
4,247 reviews
Search Southwest flights
American AirlinesPriceFrom $157Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $159Free CancellationRating
7.4
8,910 reviews
Search United 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 Dallas to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Dallas to Chicago for you.

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

momondo does allow users to show only those flights to Chicago from Dallas which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Dallas to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Dallas to Chicago.

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

Yes. momondo can track prices for Dallas to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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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
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport