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Cheap flights from the United States to Chicago from $44

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from the United States to Chicago departing on 12/20. 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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Find the cheapest flights from the United States to Chicago

Recent round-trip flight deals from the United States to Chicago

Enter your travel dates to find the best prices.
Frontier Logo
9:10 pm - 10:12 pmATL-MDW
2h 02mnonstop
Frontier Logo
8:42 pm - 11:48 pmMDW-ATL
2h 06mnonstop
$74Frontier
Find Deal
Fri, Dec 5 - Fri, Dec 12
Frontier Logo
5:07 pm - 6:08 pmATL-MDW
2h 01mnonstop
Frontier Logo
6:00 am - 9:18 amMDW-ATL
2h 18mnonstop
$78Frontier
Find Deal
Thu, Dec 11 - Sun, Dec 28
Frontier Logo
8:15 am - 9:17 amATL-MDW
2h 02mnonstop
Frontier Logo
6:00 am - 9:18 amMDW-ATL
2h 18mnonstop
$79Frontier
Find Deal
Tue, Dec 2 - Sat, Dec 6
Frontier Logo
9:30 pm - 10:33 pmATL-MDW
2h 03mnonstop
Frontier Logo
6:05 am - 9:22 amMDW-ATL
2h 17mnonstop
$80Frontier
Find Deal
Sun, Nov 23 - Wed, Nov 26
Frontier Logo
9:10 pm - 10:12 pmATL-MDW
2h 02mnonstop
Frontier Logo
6:00 am - 9:18 amMDW-ATL
2h 18mnonstop
$81Frontier
Find Deal
Fri, Dec 12 - Sun, Dec 28
Southwest Logo
7:45 pm - 10:10 pmHOU-MDW
2h 25mnonstop
Southwest Logo
6:15 am - 9:15 amMDW-HOU
3h 00mnonstop
$117Southwest
Find Deal
Wed, Dec 31 - Tue, Jan 6
Multiple Airlines Logo
11:30 am - 1:01 pmEWR-MDW
2h 31mnonstop
Multiple Airlines Logo
2:59 pm - 11:59 pmMDW-EWR
8h 00m1 stop
$122Multiple Airlines
Find Deal
Thu, Dec 11 - Sat, Dec 13
Southwest Logo
3:00 pm - 7:05 pmHOU-MDW
4h 05m1 stop
Southwest Logo
7:55 pm - 10:40 pmMDW-HOU
2h 45mnonstop
$127Southwest
Find Deal
Wed, Dec 24 - Tue, Jan 6
Southwest Logo
8:20 am - 12:40 pmHOU-MDW
4h 20m1 stop
Southwest Logo
8:35 pm - 11:20 pmMDW-HOU
2h 45mnonstop
$154Southwest
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Thu, Nov 27 - Wed, Dec 3
Southwest Logo
3:35 pm - 7:45 pmHOU-MDW
4h 10m1 stop
Southwest Logo
8:35 pm - 11:20 pmMDW-HOU
2h 45mnonstop
$158Southwest
Find Deal
Mon, Nov 24 - Tue, Dec 2

Southwest flights from United States to Chicago Midway Airport

Our best Southwest deals on United States to Chicago Midway Airport flight tickets
Southwest
Jan 8
HOU8:30 pmHouston Hobby
2h 25m
MDW10:55 pmChicago Midway
Jan 12
MDW8:55 amChicago Midway
2h 55m
HOU11:50 amHouston Hobby
$117
Find similar
Southwest
Dec 24
HOU3:00 pmHouston Hobby
4h 05m
1 stop
MDW7:05 pmChicago Midway
Jan 6
MDW7:55 pmChicago Midway
2h 45m
HOU10:40 pmHouston Hobby
$127
Find similar
Southwest
Dec 11
LGA6:00 amNew York LaGuardia
2h 30m
MDW7:30 amChicago Midway
Dec 15
MDW7:15 pmChicago Midway
2h 05m
LGA10:20 pmNew York LaGuardia
$137
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Frontier flights from United States to Chicago Midway Airport

Our best Frontier deals on United States to Chicago Midway Airport flight tickets
Frontier
Dec 5
ATL9:10 pmAtlanta Hartsfield-Jackson
2h 02m
MDW10:12 pmChicago Midway
Dec 12
MDW8:42 pmChicago Midway
2h 06m
ATL11:48 pmAtlanta Hartsfield-Jackson
$74
Find similar
Frontier
Nov 21
ATL9:40 pmAtlanta Hartsfield-Jackson
2h 03m
MDW10:43 pmChicago Midway
Nov 25
MDW6:05 amChicago Midway
2h 17m
ATL9:22 amAtlanta Hartsfield-Jackson
$78
Find similar
Frontier
Nov 23
ATL9:30 pmAtlanta Hartsfield-Jackson
2h 03m
MDW10:33 pmChicago Midway
Nov 26
MDW6:05 amChicago Midway
2h 17m
ATL9:22 amAtlanta Hartsfield-Jackson
$79
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from United States to Chicago Midway Airport 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 November 13, 2025.
Use the filters below to find and compare flights from the United States to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

AtlantaChicago

ATL - MDW

ATLMDW

Atlanta Hartsfield-Jackson

Fri 12/5

9:10 pm-10:12 pm

Nonstop2h 02m

Chicago Midway

Fri 12/12

8:42 pm-11:48 pm

Nonstop2h 06m

$74

AtlantaChicago

ATL - MDW

ATLMDW

Atlanta Hartsfield-Jackson

Thu 12/11

5:07 pm-6:08 pm

Nonstop2h 01m

Chicago Midway

Sun 12/28

6:00 am-9:18 am

Nonstop2h 18m

$78

AtlantaChicago

ATL - MDW

ATLMDW

Atlanta Hartsfield-Jackson

Tue 12/2

8:15 am-9:17 am

Nonstop2h 02m

Chicago Midway

Sat 12/6

6:00 am-9:18 am

Nonstop2h 18m

$79

AtlantaChicago

ATL - MDW

ATLMDW

Atlanta Hartsfield-Jackson

Sun 11/23

9:30 pm-10:33 pm

Nonstop2h 03m

Chicago Midway

Wed 11/26

6:05 am-9:22 am

Nonstop2h 17m

$80

AtlantaChicago

ATL - MDW

ATLMDW

Atlanta Hartsfield-Jackson

Fri 12/12

9:10 pm-10:12 pm

Nonstop2h 02m

Chicago Midway

Sun 12/28

6:00 am-9:18 am

Nonstop2h 18m

$81

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 12/31

7:45 pm-10:10 pm

Nonstop2h 25m

Chicago Midway

Tue 1/6

6:15 am-9:15 am

Nonstop3h 00m

$117

NewarkChicago

EWR - MDW

EWRMDW

Newark

Thu 12/11

11:30 am-1:01 pm

Nonstop2h 31m

Chicago Midway

Sat 12/13

2:59 pm-11:59 pm

1 stop8h 00m

$122

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 12/24

3:00 pm-7:05 pm

1 stop4h 05m

Chicago Midway

Tue 1/6

7:55 pm-10:40 pm

Nonstop2h 45m

$127

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Thu 11/27

8:20 am-12:40 pm

1 stop4h 20m

Chicago Midway

Wed 12/3

8:35 pm-11:20 pm

Nonstop2h 45m

$154

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Mon 11/24

3:35 pm-7:45 pm

1 stop4h 10m

Chicago Midway

Tue 12/2

8:35 pm-11:20 pm

Nonstop2h 45m

$158

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 United States to Chicago Midway Airport

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 Midway Airport?

The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from United States, with most prices found around $212. If you are unable to visit Chicago Midway Airport during the month of January, then departing from United States during the month February is also very affordable. Most momondo users find prices during this month for around $221.

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

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from United States. The lowest ticket price found for a Wednesday departure recently was $275. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from United States because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $422.

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

Flying to Chicago Midway Airport from United States in the evening is the least expensive time of day to depart. momondo users have found prices as low as $243 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $360. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest United States to Chicago Midway flight route?

Fly from Newark to Chicago Midway for the best United States - Chicago Midway flight prices

What cabin class options are available on United States to Chicago Midway flights?

There are 3 cabin classes available to choose from on United States to Chicago Midway 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 United States to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between United States to Chicago Midway Airport.

Cheap United States to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from United States to Chicago Midway Airport

Best Price Found

$59

Fastest flight time

1h 54m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from United States in the past 72 hours is $59. The best round-trip flight deal from United States to Chicago Midway Airport found on momondo in the last 72 hours is $71.
The fastest flight from United States to Chicago Midway Airport takes 1h 54m
Direct flights go from United States to Chicago Midway Airport every day.
Search flight deals

  • When did momondo last update prices for flights from United States to Chicago Midway Airport?

    Prices for flights from United States to Chicago Midway Airport are updated daily.

  • How many operators does momondo search for flights from United States to Chicago Midway Airport?

  • How old do you have to be to fly from United States to Chicago Midway Airport?

    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 United States to Chicago Midway Airport.

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

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from United States to Chicago Midway Airport?

Best airlines flying from United States to Chicago Midway Airport

Compare and see reviews for airlines that fly from United States to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $63Free CancellationRating
5.8
3,114 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $67Free CancellationRating
6.3
8,139 reviews
Search Spirit Airlines flights
DeltaPriceFrom $111Free CancellationRating
7.9
8,007 reviews
Search Delta flights
SouthwestPriceFrom $117Free CancellationRating
8.0
4,236 reviews
Search Southwest flights
United AirlinesPriceFrom $133Free CancellationRating
7.4
9,015 reviews
Search United Airlines flights
American AirlinesPriceFrom $197Free CancellationRating
7.2
11,050 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
Portage
Lansing
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 United States to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from United States to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

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

How can momondo help me find flights from United States to Chicago?

Once all potential United States to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

If you are not ready to book a flight from United States to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

An easier way to manage your Chicago Midway Airport trip

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