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Flights to Chicago

$89 Cheap flights to Chicago

1 adult
1 adult, Economy, 0 bags

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Cheap round-trip flights

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Frontier Logo
11:54 am - 1:30 pmPHL  Philadelphia-ORD Chicago O'Hare Intl
2h 36mnonstop
Frontier Logo
7:25 am - 10:49 amORD  Chicago O'Hare Intl-PHL Philadelphia
2h 24mnonstop
$166Frontier
Mon, Sep 21 - Thu, Sep 24
Frontier Logo
9:09 pm - 10:39 pmPHL  Philadelphia-ORD Chicago O'Hare Intl
2h 30mnonstop
Frontier Logo
4:41 pm - 8:04 pmORD  Chicago O'Hare Intl-PHL Philadelphia
2h 23mnonstop
$167Frontier
Thu, Oct 22 - Sun, Oct 25
United Airlines Logo
8:30 am - 9:45 amDCA  Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl
2h 15mnonstop
United Airlines Logo
4:00 pm - 7:09 pmORD  Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National
2h 09mnonstop
$177United Airlines
Thu, Oct 1 - Thu, Oct 1
United Airlines Logo
11:57 am - 1:13 pmDCA  Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl
2h 16mnonstop
United Airlines Logo
5:59 am - 8:54 amORD  Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National
1h 55mnonstop
$177United Airlines
Wed, Sep 23 - Thu, Sep 24
American Airlines Logo
3:58 pm - 5:28 pmDCA  Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl
2h 30mnonstop
American Airlines Logo
6:55 am - 9:59 amORD  Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National
2h 04mnonstop
$177American Airlines
Sat, Sep 26 - Sat, Oct 3
American Airlines Logo
6:30 am - 7:58 amDCA  Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl
2h 28mnonstop
American Airlines Logo
8:55 pm - 11:59 pmORD  Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National
2h 04mnonstop
$177American Airlines
Thu, Sep 17 - Sat, Sep 19
JetBlue Logo
6:55 am - 8:49 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 54mnonstop
JetBlue Logo
8:04 pm - 11:59 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 55mnonstop
$184JetBlue
Tue, Oct 6 - Thu, Oct 8
Multiple Airlines Logo
9:59 pm - 3:30 pmBWI  Baltimore/Washington-ORD Chicago O'Hare Intl
42h 31m2 stops Tampa Fort Lauderdale
Multiple Airlines Logo
6:00 am - 9:03 amORD  Chicago O'Hare Intl-BWI Baltimore/Washington
2h 03mnonstop
$193Multiple Airlines
Mon, Oct 12 - Mon, Oct 19
JetBlue Logo
7:00 am - 8:48 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 48mnonstop
JetBlue Logo
9:38 am - 1:06 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 28mnonstop
$198JetBlue
Thu, Sep 17 - Mon, Sep 21
Multiple Airlines Logo
11:54 am - 1:30 pmPHL  Philadelphia-ORD Chicago O'Hare Intl
2h 36mnonstop
Multiple Airlines Logo
7:11 am - 11:18 pmORD  Chicago O'Hare Intl-PHL Philadelphia
15h 07m3 stops Fort Lauderdale Tampa Atlanta Hartsfield-Jackson
$206Multiple Airlines
Mon, Oct 5 - Wed, Oct 7

momondo Fare Finder

 
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

PhiladelphiaChicago

PHL Philadelphia - ORD Chicago O'Hare Intl

PHLORD

Philadelphia

Mon 9/21

11:54 am-1:30 pm

Nonstop2h 36m

Chicago O'Hare Intl

Thu 9/24

7:25 am-10:49 am

Nonstop2h 24m

$166

PhiladelphiaChicago

PHL Philadelphia - ORD Chicago O'Hare Intl

PHLORD

Philadelphia

Thu 10/22

9:09 pm-10:39 pm

Nonstop2h 30m

Chicago O'Hare Intl

Sun 10/25

4:41 pm-8:04 pm

Nonstop2h 23m

$167

Washington, D.C.Chicago

DCA Washington, D.C. Reagan-National - ORD Chicago O'Hare Intl

DCAORD

Washington, D.C. Reagan-National

Thu 10/1

8:30 am-9:45 am

Nonstop2h 15m

Chicago O'Hare Intl

Thu 10/1

4:00 pm-7:09 pm

Nonstop2h 09m

$177
Quickest round-trip

Washington, D.C.Chicago

DCA Washington, D.C. Reagan-National - ORD Chicago O'Hare Intl

DCAORD

Washington, D.C. Reagan-National

Wed 9/23

11:57 am-1:13 pm

Nonstop2h 16m

Chicago O'Hare Intl

Thu 9/24

5:59 am-8:54 am

Nonstop1h 55m

$177

Washington, D.C.Chicago

DCA Washington, D.C. Reagan-National - ORD Chicago O'Hare Intl

DCAORD

Washington, D.C. Reagan-National

Sat 9/26

3:58 pm-5:28 pm

Nonstop2h 30m

Chicago O'Hare Intl

Sat 10/3

6:55 am-9:59 am

Nonstop2h 04m

$177

Washington, D.C.Chicago

DCA Washington, D.C. Reagan-National - ORD Chicago O'Hare Intl

DCAORD

Washington, D.C. Reagan-National

Thu 9/17

6:30 am-7:58 am

Nonstop2h 28m

Chicago O'Hare Intl

Sat 9/19

8:55 pm-11:59 pm

Nonstop2h 04m

$177

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Tue 10/6

6:55 am-8:49 am

Nonstop2h 54m

Chicago O'Hare Intl

Thu 10/8

8:04 pm-11:59 pm

Nonstop2h 55m

$184

BaltimoreChicago

BWI Baltimore/Washington - ORD Chicago O'Hare Intl

BWIORD

Baltimore/Washington

Mon 10/12

9:59 pm-3:30 pm

2 stops42h 31m

Chicago O'Hare Intl

Mon 10/19

6:00 am-9:03 am

Nonstop2h 03m

$193

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Thu 9/17

7:00 am-8:48 am

Nonstop2h 48m

Chicago O'Hare Intl

Mon 9/21

9:38 am-1:06 pm

Nonstop2h 28m

$198

PhiladelphiaChicago

PHL Philadelphia - ORD Chicago O'Hare Intl

PHLORD

Philadelphia

Mon 10/5

11:54 am-1:30 pm

Nonstop2h 36m

Chicago O'Hare Intl

Wed 10/7

7:11 am-11:18 pm

3 stops15h 07m

$206

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 $179. 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 $185.

What is the absolute cheapest flight to Chicago?

In the past two weeks, users have booked deals to Chicago for $49/person, which is 81% 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 $326. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from United States to Chicago for around $410.

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 $317. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $372.

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 $242 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 $177 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 ANGELESSeptember20% cheaperFlying from Los Angeles to Chicago costs on average just $289 in September
MOST EXPENSIVE MONTH TO FLY TO CHICAGO FROM LOS ANGELESJune18% more expensiveIt costs about $424 for flights to Chicago from Los Angeles in June
MOST POPULAR MONTH TO FLY TO CHICAGO FROM LOS ANGELESJuly220% 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

$89

Best Round-Trip Price

$166

Fastest flight time

2h 15m

Popular in

July
The best one-way flight price to Chicago from United States in the last 5 days is $89 (Washington, D.C. Reagan-National to Chicago O'Hare Intl).
Search Deals
The best round-trip flight price to Chicago from United States in the last 5 days is $166 (Philadelphia to Chicago O'Hare Intl).
Search Deals
The fastest flight to Chicago from United States takes 2h 15m (Washington, D.C. Dulles Intl to Chicago O'Hare Intl).
Search Deals
July has the highest demand for flights to Chicago, with a 7% 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 83 days out, which is when prices tend to be around $260. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $179.

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 $160/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 August 2026, there are 59 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
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Porter
Crown Point
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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