Find the best package deals
Bundle and save when you book your stay along with flight

Origin
Destination
Departing
Returning
- 1 Room +

Hotel Check in and Check out

Find cheap hotel deals & accommodation rates around the world
Best Price • Free Cancellation • Zero Booking Fees

Going to
Check in - Check out
- 1 Room +


Room 1:
Adult(s)
Child(ren)

Room 1:
Adult(s)
Child(ren)

Find Flights to Chicago from Boston

  • Round Trip
  • One Way
  • Multi-trip
Flying From
Flying To
Departing

 

Good to Know - Flights from Los Angeles to Chicago

  • Low Season:
  • March
  • Best time to beat the crowds
  • 3%
  • expected price decrease
  • High Season:
  • August
  • Most popular time to fly
  • 10%
  • expected price decrease
  • Average Price:
  • $256
  • (avg. price over the last 2 weeks)
  • Good Deal:
  • $206
  • or less (round trip)

The cheapest flight route between the cities is:
LAX - ORD Los Angeles Los Angeles Intl - Chicago

The most popular route is:
LAX - ORD



Cheapest flights and Hotels to Chicago from Boston


Aegean Airlines

$206 USD

Select

  • Sun, Dec 6th PHL
    Philadelphia

  • ORD 02h 21m
    Chicago
  • Sun, Dec 13th ORD
    Chicago

  • PHL 02h 03m
    Philadelphia

Sun, 18th Oct 1:27 PM

Alaska Airlines

$359 USD

Select

  • Sat, Dec 26th FAT
    Fresno

  • ORD 23h 15m
    Chicago
  • Fri, Jan 1st ORD
    Chicago

  • FAT 09h 45m
    Fresno

Sun, 18th Oct 1:25 PM

Aegean Airlines

$106 USD

Select

  • Fri, Jan 8th LAX
    Los Angeles

  • ORD 03h 48m
    Chicago
  • Mon, Jan 11th ORD
    Chicago

  • LAX 04h 22m
    Los Angeles

Tue, 20th Oct 6:10 PM

Aegean Airlines

$298 USD

Select

  • Wed, Nov 25th MDT
    Harrisburg

  • ORD 02h 07m
    Chicago
  • Fri, Jan 1st ORD
    Chicago

  • MDT 01h 45m
    Harrisburg

Sun, 18th Oct 5:24 PM

$151 USD

Select

  • Mon, Nov 23rd SEA
    Seattle

  • ORD 10h 49m
    Chicago
  • Mon, Dec 7th ORD
    Chicago

  • SEA 04h 40m
    Seattle

Wed, 21st Oct 12:36 AM

Aegean Airlines

$80 USD

Select

  • Sun, Dec 6th DEN
    Denver

  • ORD 02h 24m
    Chicago
  • Sun, Dec 13th ORD
    Chicago

  • DEN 02h 40m
    Denver

Sun, 18th Oct 1:21 PM

Aegean Airlines

$238 USD

Select

  • Sat, Dec 5th ROC
    Rochester

  • ORD 01h 52m
    Chicago
  • Tue, Jan 5th ORD
    Chicago

  • ROC 01h 34m
    Rochester

Tue, 20th Oct 9:19 PM

Aegean Airlines

$118 USD

Select

  • Sun, Dec 6th MCO
    Orlando

  • ORD 02h 59m
    Chicago
  • Mon, Dec 14th ORD
    Chicago

  • MCO 02h 38m
    Orlando

Tue, 20th Oct 8:29 AM

Aegean Airlines

$165 USD

Select

  • Tue, Dec 8th CLT
    Charlotte

  • ORD 01h 59m
    Chicago
  • Tue, Dec 15th ORD
    Chicago

  • CLT 01h 47m
    Charlotte

Sun, 18th Oct 12:51 PM

Aegean Airlines

$378 USD

Select

  • Sat, Dec 26th FSD
    Sioux Falls

  • ORD 01h 47m
    Chicago
  • Fri, Jan 1st ORD
    Chicago

  • FSD 01h 43m
    Sioux Falls

Sun, 18th Oct 9:33 PM

Aegean Airlines

$162 USD

Select

  • Tue, Dec 8th RSW
    Fort Myers

  • ORD 03h 07m
    Chicago
  • Tue, Dec 15th ORD
    Chicago

  • RSW 02h 56m
    Fort Myers

Mon, 19th Oct 12:51 AM

Aegean Airlines

$84 USD

Select

  • Tue, Dec 8th IAH
    Houston

  • ORD 02h 30m
    Chicago
  • Sun, Dec 13th ORD
    Chicago

  • IAH 02h 38m
    Houston

Sun, 18th Oct 11:49 PM

Aegean Airlines

$146 USD

Select

  • Fri, Nov 20th IAD
    Washington

  • ORD 02h 04m
    Chicago
  • Sat, Dec 5th ORD
    Chicago

  • IAD 01h 44m
    Washington

Mon, 19th Oct 10:51 PM

Aegean Airlines

$84 USD

Select

  • Sun, Dec 6th DFW
    Dallas

  • ORD 02h 14m
    Chicago
  • Sun, Dec 13th ORD
    Chicago

  • DFW 02h 23m
    Dallas

Sun, 18th Oct 1:20 PM

Aegean Airlines

$278 USD

Select

  • Fri, Jan 1st CHO
    Charlottesville

  • ORD 01h 58m
    Chicago
  • Thu, Jan 7th ORD
    Chicago

  • CHO 01h 52m
    Charlottesville

Tue, 20th Oct 5:19 PM

Alaska Airlines

$225 USD

Select

  • Fri, Jan 1st LSE
    La Crosse

  • ORD 01h 16m
    Chicago
  • Wed, Jan 6th ORD
    Chicago

  • LSE 01h 08m
    La Crosse

Tue, 20th Oct 7:06 PM

Aegean Airlines

$166 USD

Select

  • Sun, Dec 6th LGA
    New York

  • ORD 02h 24m
    Chicago
  • Sun, Dec 13th ORD
    Chicago

  • LGA 02h 03m
    New York

Sun, 18th Oct 1:19 PM

Aegean Airlines

$84 USD

Select

  • Thu, Jan 7th PHX
    Phoenix

  • ORD 03h 25m
    Chicago
  • Sun, Jan 10th ORD
    Chicago

  • PHX 03h 59m
    Phoenix

Mon, 19th Oct 12:12 AM

Alaska Airlines

$251 USD

Select

  • Thu, Dec 31st SNA
    Santa Ana

  • ORD 04h 13m
    Chicago
  • Thu, Jan 7th ORD
    Chicago

  • SNA 04h 15m
    Santa Ana

Sun, 18th Oct 11:21 PM

Aegean Airlines

$79 USD

Select

  • Thu, Jan 7th FLL
    Fort Lauderdale

  • ORD 03h 14m
    Chicago
  • Sun, Jan 10th ORD
    Chicago

  • FLL 03h 00m
    Fort Lauderdale

Sun, 18th Oct 8:25 PM

Aegean Airlines

$266 USD

Select

  • Sun, Dec 6th SLC
    Salt Lake City

  • ORD 03h 04m
    Chicago
  • Sun, Dec 13th ORD
    Chicago

  • SLC 03h 26m
    Salt Lake City

Sun, 18th Oct 1:49 PM

Aegean Airlines

$96 USD

Select

  • Thu, Nov 19th BNA
    Nashville

  • ORD 01h 47m
    Chicago
  • Mon, Dec 7th ORD
    Chicago

  • BNA 01h 24m
    Nashville

Sun, 18th Oct 10:18 PM

$271 USD

Select

  • Tue, Dec 1st MSN
    Madison

  • ORD 15h 53m
    Chicago
  • Tue, Dec 8th ORD
    Chicago

  • MSN 08h 12m
    Madison

Mon, 19th Oct 5:18 PM

Aegean Airlines

$126 USD

Select

  • Tue, Dec 1st BUF
    Buffalo

  • ORD 01h 57m
    Chicago
  • Sat, Dec 5th ORD
    Chicago

  • BUF 01h 38m
    Buffalo

Sun, 18th Oct 7:24 AM

Aegean Airlines

$84 USD

Select

  • Sun, Dec 6th TPA
    Tampa

  • ORD 02h 50m
    Chicago
  • Sun, Dec 13th ORD
    Chicago

  • TPA 02h 39m
    Tampa

Sun, 18th Oct 1:38 PM

Alaska Airlines

$255 USD

Select

  • Tue, Dec 8th BUR
    Burbank

  • ORD 09h 30m
    Chicago
  • Tue, Dec 15th ORD
    Chicago

  • BUR 08h 10m
    Burbank

Sun, 18th Oct 10:15 AM

Aegean Airlines

$106 USD

Select

  • Fri, Jan 8th MSP
    Minneapolis

  • ORD 01h 19m
    Chicago
  • Sun, Jan 10th ORD
    Chicago

  • MSP 01h 22m
    Minneapolis

Mon, 19th Oct 9:54 PM

$370 USD

Select

  • Wed, Nov 18th ANC
    Anchorage

  • ORD 14h 12m
    Chicago
  • Tue, Dec 8th ORD
    Chicago

  • ANC 15h 33m
    Anchorage

Sun, 18th Oct 1:55 PM

Aegean Airlines

$118 USD

Select

  • Sun, Dec 6th BOS
    Boston

  • ORD 02h 42m
    Chicago
  • Sun, Dec 13th ORD
    Chicago

  • BOS 02h 14m
    Boston

Sun, 18th Oct 1:22 PM

Aegean Airlines

$196 USD

Select

  • Sun, Dec 6th DCA
    Washington

  • ORD 02h 06m
    Chicago
  • Sun, Dec 13th ORD
    Chicago

  • DCA 01h 41m
    Washington

Sun, 18th Oct 1:24 PM

Aegean Airlines

$226 USD

Select

  • Sun, Dec 6th JAX
    Jacksonville

  • ORD 02h 29m
    Chicago
  • Thu, Dec 10th ORD
    Chicago

  • JAX 02h 10m
    Jacksonville

Tue, 20th Oct 5:26 AM

Alaska Airlines

$265 USD

Select

  • Sun, Jan 3rd CHS
    Charleston

  • ORD 02h 33m
    Chicago
  • Sun, Jan 3rd ORD
    Chicago

  • CHS 05h 31m
    Charleston

Sun, 18th Oct 10:04 PM

Aegean Airlines

$166 USD

Select

  • Sun, Dec 6th CMH
    Columbus

  • ORD 01h 28m
    Chicago
  • Sun, Dec 13th ORD
    Chicago

  • CMH 01h 20m
    Columbus

Sun, 18th Oct 1:49 PM

Alaska Airlines

$301 USD

Select

  • Wed, Dec 30th ORF
    Norfolk

  • ORD 04h 35m
    Chicago
  • Sun, Jan 3rd ORD
    Chicago

  • ORF 02h 11m
    Norfolk

Mon, 19th Oct 11:05 PM

Aegean Airlines

$367 USD

Select

  • Sun, Jun 6th SAT
    San Antonio

  • ORD 04h 51m
    Chicago
  • Thu, Jun 10th ORD
    Chicago

  • SAT 02h 54m
    San Antonio

Mon, 19th Oct 7:32 PM

Aegean Airlines

$246 USD

Select

  • Sun, Dec 6th BDL
    Hartford

  • ORD 02h 43m
    Chicago
  • Sun, Dec 13th ORD
    Chicago

  • BDL 02h 02m
    Hartford

Sun, 18th Oct 1:59 PM

Aegean Airlines

$171 USD

Select

  • Thu, Dec 3rd SMF
    Sacramento

  • ORD 10h 58m
    Chicago
  • Tue, Dec 8th ORD
    Chicago

  • SMF 10h 36m
    Sacramento

Tue, 20th Oct 9:51 PM

Aegean Airlines

$316 USD

Select

  • Thu, May 27th TUS
    Tucson

  • ORD 03h 35m
    Chicago
  • Fri, Jun 4th ORD
    Chicago

  • TUS 05h 25m
    Tucson

Sun, 18th Oct 11:02 AM

Alaska Airlines

$85 USD

Select

  • Sun, Dec 6th AUS
    Austin

  • ORD 02h 49m
    Chicago
  • Sun, Dec 13th ORD
    Chicago

  • AUS 02h 35m
    Austin

Sun, 18th Oct 1:42 PM

Aegean Airlines

$103 USD

Select

  • Sun, Nov 22nd DEC
    Decatur

  • ORD 01h 05m
    Chicago
  • Tue, Dec 1st ORD
    Chicago

  • DEC 01h 05m
    Decatur

Tue, 20th Oct 6:17 PM

Aegean Airlines

$295 USD

Select

  • Tue, Dec 1st MRY
    Monterey Carmel

  • ORD 06h 20m
    Chicago
  • Sat, Dec 5th ORD
    Chicago

  • MRY 05h 49m
    Monterey Carmel

Tue, 20th Oct 6:17 PM

Alaska Airlines

$237 USD

Select

  • Thu, Jan 7th SJC
    San Jose

  • ORD 09h 57m
    Chicago
  • Sun, Jan 10th ORD
    Chicago

  • SJC 09h 52m
    San Jose

Wed, 21st Oct 1:55 AM

Aegean Airlines

$186 USD

Select

  • Thu, Jan 7th ALB
    Albany

  • ORD 02h 39m
    Chicago
  • Sun, Jan 10th ORD
    Chicago

  • ALB 01h 55m
    Albany

Sun, 18th Oct 9:40 PM

Aegean Airlines

$146 USD

Select

  • Thu, Jan 7th PIT
    Pittsburgh

  • ORD 01h 31m
    Chicago
  • Sun, Jan 10th ORD
    Chicago

  • PIT 01h 22m
    Pittsburgh

Sun, 18th Oct 9:40 PM

Aegean Airlines

$84 USD

Select

  • Fri, Jan 8th MIA
    Miami

  • ORD 03h 20m
    Chicago
  • Mon, Jan 11th ORD
    Chicago

  • MIA 03h 06m
    Miami

Tue, 20th Oct 9:34 PM

Spirit Airlines

$297 USD

Select

  • Sun, Nov 29th ATL
    Atlanta

  • ORD 02h 08m
    Chicago
  • Sun, Dec 6th ORD
    Chicago

  • ATL 02h 04m
    Atlanta

Mon, 19th Oct 8:38 PM

Aegean Airlines

$266 USD

Select

  • Sun, Dec 6th PDX
    Portland

  • ORD 05h 20m
    Chicago
  • Sun, Dec 13th ORD
    Chicago

  • PDX 09h 33m
    Portland

Sun, 18th Oct 1:51 PM

Alaska Airlines

$398 USD

Select

  • Sat, Jan 2nd ASE
    Aspen

  • ORD 15h 46m
    Chicago
  • Wed, Jan 6th ORD
    Chicago

  • ASE 13h 48m
    Aspen

Sun, 18th Oct 6:37 PM

Aegean Airlines

$552 USD

Select

  • Sat, Jan 2nd EGE
    Vail Eagle

  • ORD 02h 40m
    Chicago
  • Wed, Jan 6th ORD
    Chicago

  • EGE 02h 59m
    Vail Eagle

Sun, 18th Oct 6:39 PM

Aegean Airlines

$118 USD

Select

  • Fri, Dec 4th ORL
    Orlando

  • ORD 02h 59m
    Chicago
  • Mon, Dec 7th ORD
    Chicago

  • ORL 02h 38m
    Orlando

Tue, 20th Oct 8:10 PM

FAQs - Booking Chicago flights

How long is the flight to Chicago?

Which airlines fly to Chicago ?

In general from United States, United Airlines, American Airlines and Delta fly the most to Chicago. The most popular route is from Los Angeles, and United Airlines, American Airlines & Alaska Airlines fly this route the most.

How does Skybooker find such low flight prices?

Skybooker processes over 2 billion travel queries annually and displays results from hundreds of airlines and third party sites, allowing it to find a variety of flight prices and options. It also displays results from 2M+ properties along with rental cars, vacation packages, activities and millions of verified reviews so users can see as many available travel options as possible.

Does Skybooker query more flight providers than competitors?

Yes, Skybooker has access to more data and information than online travel agencies and consistently outperforms the competition in accuracy, globally.

Airlines flying to Chicago

Aegean Airlines, Alaska Airlines, Spirit Airlines, Frontier Airlines

Read top articles from Travelogue

Top Tips for Finding Cheap Flights to Chicago

Looking for cheap airfare to Chicago? 30% of our users found round-trip tickets to Chicago for the following prices or less. If you are looking at getting the best of the deals, you can follow these tips. Book at least 4 weeks before departure in order to get a below-average price. High/Peak season is considered to be July and August. The cheapest month to fly to Chicago is February or March. You can enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals. For flights to Chicago, one can choose from various flight providers. To be able to get the best of fares, one needs to plan their trips well in advance to avoid surged fares. Ensure you compare fares before finalizing on one flight provider. This would help you in understanding the fare trends, thus getting you the best deal. Planning your commute to the airport is equally important. Booking a cab, or taking a train to the airport should be planned with ample time in hand to avoid any last moment delays or mishaps. If traveling with elders, it is good to pre-book services like a wheel-chair at the airport or any other services that one would need at the airport. This would help save time.


Flights to Chicago

Los Angeles to Chicago Information

Flights Arrive in Chicago (ORD)
Flights Depart from Los Angeles Intl - LAX
Airlines Aegean Airlines, Alaska Airlines, Spirit Airlines, Frontier Airlines