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Flights to Chicago

$50 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 5/17. 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

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Multiple Airlines Logo
8:55 am - 11:40 am
DFW
-
ORD
2h 45mnonstop
Multiple Airlines Logo
8:34 pm - 11:07 pm
ORD
-
DFW
2h 33mnonstop
$100Multiple Airlines
Tue, Jun 2 - Tue, Jun 23
Frontier Logo
1:19 pm - 4:10 pm
DFW
-
ORD
2h 51mnonstop
Frontier Logo
9:34 pm - 12:19 am
ORD
-
DFW
2h 45mnonstop
$101Frontier
Sat, Aug 15 - Tue, Aug 18
Spirit Airlines Logo
9:38 am - 12:04 pm
DFW
-
ORD
2h 26mnonstop
Spirit Airlines Logo
8:00 am - 10:32 am
ORD
-
DFW
2h 32mnonstop
$103Spirit Airlines
Sun, May 17 - Tue, May 19
Spirit Airlines Logo
12:38 pm - 3:03 pm
DFW
-
ORD
2h 25mnonstop
Spirit Airlines Logo
9:17 am - 11:57 am
ORD
-
DFW
2h 40mnonstop
$109Spirit Airlines
Tue, May 12 - Sat, May 23
JetBlue Logo
7:35 pm - 9:39 pm
BOS
-
ORD
3h 04mnonstop
JetBlue Logo
9:49 am - 1:20 pm
ORD
-
BOS
2h 31mnonstop
$147JetBlue
Tue, Apr 28 - Tue, May 12
Delta Logo
12:00 pm - 1:54 pm
BOS
-
ORD
2h 54mnonstop
Delta Logo
7:00 am - 10:35 am
ORD
-
BOS
2h 35mnonstop
$153Delta
Sat, May 16 - Wed, May 20
Delta Logo
7:35 am - 9:27 am
BOS
-
ORD
2h 52mnonstop
Delta Logo
7:16 pm - 10:50 pm
ORD
-
BOS
2h 34mnonstop
$155Delta
Wed, May 13 - Wed, May 13
JetBlue Logo
7:05 am - 8:48 am
JFK
-
ORD
2h 43mnonstop
JetBlue Logo
6:27 pm - 10:03 pm
ORD
-
JFK
2h 36mnonstop
$172JetBlue
Wed, Aug 12 - Wed, Aug 12
United Airlines Logo
11:08 am - 12:26 pm
BWI
-
ORD
2h 18mnonstop
United Airlines Logo
11:10 am - 2:13 pm
ORD
-
BWI
2h 03mnonstop
$198United Airlines
Wed, Apr 29 - Sat, May 2
United Airlines Logo
6:15 am - 7:26 am
IAD
-
ORD
2h 11mnonstop
United Airlines Logo
9:35 pm - 12:33 am
ORD
-
IAD
1h 58mnonstop
$219United Airlines
Thu, May 7 - Mon, May 18

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 10, 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 6/2

8:55 am-11:40 am

Nonstop2h 45m

Chicago O'Hare Intl

Tue 6/23

8:34 pm-11:07 pm

Nonstop2h 33m

$100

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Sat 8/15

1:19 pm-4:10 pm

Nonstop2h 51m

Chicago O'Hare Intl

Tue 8/18

9:34 pm-12:19 am

Nonstop2h 45m

$101

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Sun 5/17

9:38 am-12:04 pm

Nonstop2h 26m

Chicago O'Hare Intl

Tue 5/19

8:00 am-10:32 am

Nonstop2h 32m

$103

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Tue 5/12

12:38 pm-3:03 pm

Nonstop2h 25m

Chicago O'Hare Intl

Sat 5/23

9:17 am-11:57 am

Nonstop2h 40m

$109

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 4/28

7:35 pm-9:39 pm

Nonstop3h 04m

Chicago O'Hare Intl

Tue 5/12

9:49 am-1:20 pm

Nonstop2h 31m

$147

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 5/16

12:00 pm-1:54 pm

Nonstop2h 54m

Chicago O'Hare Intl

Wed 5/20

7:00 am-10:35 am

Nonstop2h 35m

$153

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 5/13

7:35 am-9:27 am

Nonstop2h 52m

Chicago O'Hare Intl

Wed 5/13

7:16 pm-10:50 pm

Nonstop2h 34m

$155

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Wed 8/12

7:05 am-8:48 am

Nonstop2h 43m

Chicago O'Hare Intl

Wed 8/12

6:27 pm-10:03 pm

Nonstop2h 36m

$172

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Wed 4/29

11:08 am-12:26 pm

Nonstop2h 18m

Chicago O'Hare Intl

Sat 5/2

11:10 am-2:13 pm

Nonstop2h 03m

$198
Quickest round-trip

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 5/7

6:15 am-7:26 am

Nonstop2h 11m

Chicago O'Hare Intl

Mon 5/18

9:35 pm-12:33 am

Nonstop1h 58m

$219

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 $56/person, which is 79% 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 Wednesday 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 $367.

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 $270. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $361.

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 $241 in September
MOST EXPENSIVE MONTH TO FLY TO CHICAGO FROM LOS ANGELESFebruary23% more expensiveIt costs about $390 for flights to Chicago from Los Angeles in February
MOST POPULAR MONTH TO FLY TO CHICAGO FROM LOS ANGELESJuly218% 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

$50

Best Round-Trip Price

$100

Fastest flight time

2h 19m

Popular in

June
The best one-way flight price to Chicago from United States in the last 72 hours is $50 (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 $100 (Dallas/Fort Worth to Chicago O'Hare Intl).
Search Deals
The fastest flight to Chicago from United States takes 2h 19m (Baltimore/Washington to Chicago O'Hare Intl).
Search Deals
June has the highest demand for flights to Chicago, with a 11% price increase on average.
Search Deals

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 64 days out, which is when prices tend to be around $242. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $171.

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 $173/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 O'Hare Intl which is in Chicago and is about 15.7 mi away from Downtown.

What’s the closest airport to Magnificent Mile?

Chicago O'Hare Intl in Chicago is the closest airport to Magnificent Mile (distance: 15.5 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
Schererville
Munster
Crown Point
Chesterton
Monticello
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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