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Flights to Chicago

$53 Cheap flights to Chicago

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight to Chicago departing on 5/27. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
12:38 pm - 3:03 pm
DFW
-
ORD
2h 25mnonstop
Multiple Airlines Logo
9:22 am - 12:09 pm
ORD
-
DFW
2h 47mnonstop
$113Multiple Airlines
Tue, May 19 - Tue, Jun 9
Frontier Logo
11:55 am - 2:12 pm
DFW
-
MDW
2h 17mnonstop
Frontier Logo
3:07 pm - 5:50 pm
MDW
-
DFW
2h 43mnonstop
$113Frontier
Tue, May 12 - Wed, May 13
Frontier Logo
1:25 pm - 4:08 pm
DFW
-
ORD
2h 43mnonstop
Frontier Logo
9:34 pm - 12:19 am
ORD
-
DFW
2h 45mnonstop
$114Frontier
Sat, Aug 15 - Tue, Aug 18
Spirit Airlines Logo
12:38 pm - 3:03 pm
DFW
-
ORD
2h 25mnonstop
Spirit Airlines Logo
8:00 am - 10:32 am
ORD
-
DFW
2h 32mnonstop
$117Spirit Airlines
Tue, May 19 - Wed, May 20
Spirit Airlines Logo
9:39 am - 12:09 pm
DFW
-
ORD
2h 30mnonstop
Spirit Airlines Logo
8:34 pm - 11:07 pm
ORD
-
DFW
2h 33mnonstop
$121Spirit Airlines
Tue, Aug 18 - Tue, Sep 1
Delta Logo
7:35 pm - 9:48 pm
JFK
-
ORD
3h 13mnonstop
Delta Logo
6:05 am - 9:26 am
ORD
-
JFK
2h 21mnonstop
$177Delta
Wed, Jun 24 - Sun, Jul 5
United Airlines Logo
7:11 pm - 8:35 pm
BWI
-
ORD
2h 24mnonstop
United Airlines Logo
9:25 pm - 12:33 am
ORD
-
BWI
2h 08mnonstop
$212United Airlines
Sat, May 23 - Tue, May 26
Delta Logo
4:24 pm - 9:46 pm
IAD
-
ORD
6h 22m
1 stop
Delta Logo
6:07 am - 12:18 pm
ORD
-
IAD
5h 11m
1 stop
$228Delta
Sat, May 23 - Tue, May 26
American Airlines Logo
2:35 pm - 9:26 pm
SFO
-
ORD
4h 51mnonstop
American Airlines Logo
9:10 pm - 11:52 pm
ORD
-
SFO
4h 42mnonstop
$273American Airlines
Sat, Jul 4 - Sat, Jul 25
American Airlines Logo
6:00 am - 12:35 pm
SFO
-
ORD
4h 35mnonstop
American Airlines Logo
6:45 am - 9:25 am
ORD
-
SFO
4h 40mnonstop
$282American Airlines
Wed, May 27 - Wed, Jun 3

momondo Fare Finder

 
Locate flights to Chicago that fit your budget, with regularly updated fares and availability. In the last 7 days, momondo users made a total of 832,500 searches and data was last updated on April 30, 2026.
Use the filters below to find and compare flights to Chicago that are best for you.

Fly from

Route

Depart

Return

Price

Cheapest round-trip

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Tue 5/19

12:38 pm-3:03 pm

Nonstop2h 25m

Chicago O'Hare Intl

Tue 6/9

9:22 am-12:09 pm

Nonstop2h 47m

$113

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Tue 5/12

11:55 am-2:12 pm

Nonstop2h 17m

Chicago Midway

Wed 5/13

3:07 pm-5:50 pm

Nonstop2h 43m

$113

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Sat 8/15

1:25 pm-4:08 pm

Nonstop2h 43m

Chicago O'Hare Intl

Tue 8/18

9:34 pm-12:19 am

Nonstop2h 45m

$114

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Tue 5/19

12:38 pm-3:03 pm

Nonstop2h 25m

Chicago O'Hare Intl

Wed 5/20

8:00 am-10:32 am

Nonstop2h 32m

$117

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Tue 8/18

9:39 am-12:09 pm

Nonstop2h 30m

Chicago O'Hare Intl

Tue 9/1

8:34 pm-11:07 pm

Nonstop2h 33m

$121

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Wed 6/24

7:35 pm-9:48 pm

Nonstop3h 13m

Chicago O'Hare Intl

Sun 7/5

6:05 am-9:26 am

Nonstop2h 21m

$177
Quickest round-trip

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Sat 5/23

7:11 pm-8:35 pm

Nonstop2h 24m

Chicago O'Hare Intl

Tue 5/26

9:25 pm-12:33 am

Nonstop2h 08m

$212

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sat 5/23

4:24 pm-9:46 pm

1 stop6h 22m

Chicago O'Hare Intl

Tue 5/26

6:07 am-12:18 pm

1 stop5h 11m

$228

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Sat 7/4

2:35 pm-9:26 pm

Nonstop4h 51m

Chicago O'Hare Intl

Sat 7/25

9:10 pm-11:52 pm

Nonstop4h 42m

$273

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 5/27

6:00 am-12:35 pm

Nonstop4h 35m

Chicago O'Hare Intl

Wed 6/3

6:45 am-9:25 am

Nonstop4h 40m

$282

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

Chicago flights insights and trends

Explore insights for your Chicago flight to craft the best travel plan

What is the cheapest month to fly to Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from United States, with most prices found around $177. If you’re not able to fly to Chicago in January, then February is your next best option. Flight prices from United States to Chicago during February average around $182.

What is the absolute cheapest flight to Chicago?

In the past two weeks, users have booked deals to Chicago for $65/person, which is 75% cheaper than the average flight to Chicago. To find the cheapest price to Chicago from your area, use momondo’s Airport-to-Airport Pricing Tool.

See prices from:

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 Saturday when prices can be found for as low as $291. 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 United States to Chicago for around $366.

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 United States to Chicago during this time can be as low as $272. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $360.

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

You are more likely to see cheaper flights to Chicago from United States when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $238 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from United States for as low as $162 on momondo.

Cheapest flights to Chicago

Find the cheapest flights to Chicago from your nearest city or airport
Find flights from Los Angeles to Chicago O'Hare Intl Airport
CHEAPEST MONTH TO FLY TO CHICAGO FROM LOS ANGELESSeptember24% cheaperFlying from Los Angeles to Chicago costs on average just $243 in September
MOST EXPENSIVE MONTH TO FLY TO CHICAGO FROM LOS ANGELESFebruary22% more expensiveIt costs about $390 for flights to Chicago from Los Angeles in February
MOST POPULAR MONTH TO FLY TO CHICAGO FROM LOS ANGELESJuly197% more users visitedMore momondo users searched in flights to Chicago from Los Angeles in July than any other month

Cheap Chicago flight deals and tips

Summary info about Chicago flight prices, duration and airlines

Best One-Way Price

$53

Best Round-Trip Price

$113

Fastest flight time

2h 17m

Popular in

June
The best one-way flight price to Chicago from United States in the last 72 hours is $53 (Dallas/Fort Worth to Chicago O'Hare Intl).
Search Deals
The best round-trip flight price to Chicago from United States in the last 72 hours is $113 (Dallas/Fort Worth to Chicago O'Hare Intl).
Search Deals
The fastest flight to Chicago from United States takes 2h 17m (Dallas/Fort Worth to Chicago Midway).
Search Deals
June has the highest demand for flights to Chicago, with a 11% price increase on average.
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Frequently asked questions about flying to Chicago

When is it best to fly to Chicago to go sightseeing?

The best time to plan to fly to Chicago to go sightseeing would be when the temperature is not unbearable and the chance of rain is only moderate. Considering those guidelines, May or June seems like the best time of year to plan your visit.

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

The best time to book a flight to Chicago from United States is 38 days out, which is when prices tend to be around $243. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $172.

Is there an alternative airport near Chicago?

Finding an alternative and possibly cheaper destination airport near Chicago is possible. If you are planning a flight to Chicago, consider booking flights to Chicago Midway Airport (9 mi from Chicago city center) or Chicago Greater Rockford Airport (79 mi from Chicago city center).

Is there a cheaper alternative to flying into Chicago?

The cheapest airport near Chicago is typically Chicago Greater Rockford Airport with an average price of $177/person. These prices vary based on where travelers are coming from. It is suggested that travelers looking to save money try momondo’s Airport-to-Airport Pricing Tool.

Are there flights to Downtown?

Yes. To go to Downtown, book a flight to Chicago Midway which is in Chicago and is about 8.9 mi away from Downtown.

What’s the closest airport to Magnificent Mile?

Chicago Midway in Chicago is the closest airport to Magnificent Mile (distance: 9.7 mi).

When did momondo last update prices for flights to Chicago?

Prices for flights to Chicago are updated daily.

How many operators does momondo search for flights to Chicago?

As of April 2026, there are 60 operators available to choose from for flights to Chicago.

How old do you have to be to fly 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 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.

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
Munster
Schererville
Crown Point
Monticello
Chesterton
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal 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 for you.

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

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

How can momondo help me find flights to Chicago?

Once you have performed a search for flights to Chicago, momondo helps you find the right flight 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.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago and alert you when they change.

An easier way to manage your Chicago trip

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