Find cheap flights to Chicago

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Boston (BOS)
Chicago (ORD)
Fri 6/18
Fri 6/25
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Travel Restriction Alert

The COVID-19 (coronavirus) outbreak may impact travel to Chicago. Current restrictions to Chicago are based on United States travel restrictions.
View current United States travel restrictions

Cheapest flights to Chicago airports

Find the cheapest flights to these Chicago airports from your nearest city or airport
Boston
Chicago Midway Airport

CHEAPEST ROUTE FROM Boston TO Chicago

Boston (BOS) to Chicago O'Hare Intl Airport (ORD)

Typically, flights to Chicago from Boston are cheaper when flying from Boston Logan Intl to Chicago O'Hare Intl, which has an average price of $146

CHEAPEST MONTH TO FLY TO CHICAGO FROM BOSTONAugust62% cheaperFlying from Boston to Chicago costs on average just $56 in August
MOST EXPENSIVE MONTH TO FLY TO CHICAGO FROM BOSTONDecember41% more expensiveIt costs about $206 for flights to Chicago from Boston in December
MOST POPULAR MONTH TO FLY TO CHICAGO FROM BOSTONOctober346% more users visitedMore momondo users searched in flights to Chicago from Boston in October than any other month

When is the best time to fly to Chicago?

What is the absolute cheapest flight to Chicago?

In the past two weeks, users have booked deals to Chicago for $36/person, which is 92% 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.

What is the cheapest month to fly to Chicago?

The month of August is, on average, the cheapest month to fly to Chicago from United States, with most prices found around $112. If you’re not able to fly to Chicago in August, then July is your next best option. Flight prices from United States to Chicago during July average around $123.

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

The best time to book a flight to Chicago from United States is 23 days out, which is when prices tend to be around $182. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $54.

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 Tuesday when prices can be found for as low as $177. 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 $217.

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 $204. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $248.

Is there a good place to hike near Chicago?

During the warmer months, hikers around the Chicago area find that parks like Grant Park are the best for taking long walks with their families and/or pets. Those looking for this type of experience are likely best suited to fly to Chicago in September or October.

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.

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 O'Hare Intl Airport (16 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 Midway Airport with an average price of $376/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.


What are the current travel restrictions for Chicago?

Currently, United States travel restrictions include travel to Chicago.

Entry restrictions

The United States has restricted the entry of all foreign nationals who have passed through or have been in China, Iran, Most European Countries (Austria, Belgium, Czech Republic, Denmark, Estonia, Finland, France, Germany, Greece, Hungary, Iceland, Italy, Latvia, Liechtenstein, Lithuania, Luxembourg, Malta, Netherlands, Norway, Poland, Portugal, Slovakia, Slovenia, Spain, Sweden, Switzerland, Monaco, San Marino, Vatican City), the UK, Ireland, Brazil and South Africa in the past 14 days. With the exception of certain travelers which includes certain family members of US citizens or permanent residents including; spouses, children (under the age of 21), parents (provided that his/her US citizen or permanent resident child is unmarried and under the age of 21), and siblings (provided that both the sibling and the US citizen or permanent resident are unmarried and under the age of 21); There is also an exception for travelers with the following visas: A-1, A-2, C-1, C-1/D, C-2, C-3, CR-1, CR-2, D, E-1 (as an employee of TECRO or TECO or the employee's immediate family members), G-1, G-2, G-3, G-4, IR-1, IR-4, IH-4, NATO-1 through NATO-4, or NATO-6 visa; Members of the US Armed Forces, spouses, and children of members of the US Armed Forces; Travelers with invitation of the USA government for a purpose related to the containment/mitigation of the Coronavirus (COVID-19); Travelers with documents issued by the US Department of Homeland Security, US Customs and Border Protection, or US Department of State indicating that the traveler is exempt from the restriction; B1 crew crewmembers that are engaged in lightering, Outer Continental Shelf (OCS) activity, wind farm activity, private air/sea crew and other similar crewmember activities; Students with an F-1 or M-1 visa and their F-2 and M-2 dependents, if they arrive from or have been in Ireland, the UK or Schengen Area in the past 14 days.

Entry requirements

All travelers, 2 years of age or older (including US citizens and transit passenger) must present a negative COVID-19 viral or antigen test result issued 72 hours prior to departure or have a proof of recovery from the virus within the last 90 days prior to boarding the plane. Travelers must complete a disclosure and attestation form before departure. Exemptions or waiver to the testing requirements may be granted by the CDC on an extremely limited basis when emergency travel (like an emergency medical evacuation) must occur to preserve someone’s life, health against a serious danger, or physical safety and testing cannot be completed before travel. US citizens and permanent residents arriving from the UK must present a medical certificate with a negative COVID-19 PCR or antigen test result issued within 72 hours prior to departure. Travelers arriving in New York State must complete the Traveler Health Form. Travelers arriving in Massachusetts must complete the Massachusetts Health Form.

Quarantine requirements

Travelers are advised to get tested 3-5 days after travel and stay home and self-quarantine for 7 days after travel. Even if they test negative, they must still stay home and self-quarantine for the full 7 days. If the test is positive, isolate to protect others from getting infected.​​ Travelers who did not get tested, are advised to stay home and self-quarantine for 10 days after travel.​

All other info

Travelers are subject to COVID-19 measures set by the state/territory of their final destination. For more information go to CDC website.

If you are planning to travel to Chicago at this time, it is recommended that you stay up to date on current restrictions and follow proper safety measures while in public.

Chicago flight deals found on momondo

Check out some of the best fares from airports in United States to Chicago found recently by users on momondo
Spirit Airlines
Sep 8
DFW6:00 amDallas/Fort Worth
2h 14m
ORD8:14 amChicago O'Hare Intl
Sep 11
ORD10:00 amChicago O'Hare Intl
2h 13m
DFW12:13 pmDallas/Fort Worth
Spirit Airlines
Sep 1
DFW3:55 pmDallas/Fort Worth
2h 28m
ORD6:23 pmChicago O'Hare Intl
Sep 8
ORD10:00 amChicago O'Hare Intl
2h 13m
DFW12:13 pmDallas/Fort Worth
Spirit Airlines
Sep 18
BOS5:53 pmBoston Logan Intl
2h 33m
ORD8:26 pmChicago O'Hare Intl
Sep 22
ORD5:00 amChicago O'Hare Intl
2h 18m
BOS7:18 amBoston Logan Intl
Spirit Airlines
Sep 11
BOS5:53 pmBoston Logan Intl
2h 33m
ORD8:26 pmChicago O'Hare Intl
Sep 14
ORD5:00 amChicago O'Hare Intl
2h 18m
BOS7:18 amBoston Logan Intl
Spirit Airlines
Sep 18
BOS5:53 pmBoston Logan Intl
2h 33m
ORD8:26 pmChicago O'Hare Intl
Sep 22
ORD5:00 amChicago O'Hare Intl
2h 18m
BOS7:18 amBoston Logan Intl
Spirit Airlines
Sep 11
BOS5:53 pmBoston Logan Intl
2h 33m
ORD8:26 pmChicago O'Hare Intl
Sep 18
ORD5:00 amChicago O'Hare Intl
2h 18m
BOS7:18 amBoston Logan Intl

Find the cheapest one-way flights to Chicago

If you're looking for one-way flights to Chicago, view some of our deals below provided by Spirit Airlines and Alaska Airlines
Spirit Airlines
Jul 16
DFW3:55 pmDallas/Fort Worth
2h 28m
ORD6:23 pmChicago O'Hare Intl
Spirit Airlines
Aug 16
DFW3:55 pmDallas/Fort Worth
2h 28m
ORD6:23 pmChicago O'Hare Intl
Spirit Airlines
Aug 28
DFW3:55 pmDallas/Fort Worth
2h 28m
ORD6:23 pmChicago O'Hare Intl

Which airlines fly to Chicago?

Here you can see a selection of the most popular and cheapest airlines for flights to Chicago

Airports near Chicago

Below you will find all the airports in Chicago along with the distance from the city center

Popular routes to Chicago

Most frequently searched flights to Chicago along with the cheapest price and shortest flight duration
Boston to Chicago Flights
Fastest flight time
2h 33m
Cheapest price
$54
Fort Lauderdale to Chicago Flights
Fastest flight time
3h 08m
Cheapest price
$60
Los Angeles to Chicago Flights
Fastest flight time
3h 57m
Cheapest price
$78
Denver to Chicago Flights
Fastest flight time
2h 18m
Cheapest price
$78
Austin to Chicago Flights
Fastest flight time
2h 35m
Cheapest price
$79
Houston to Chicago Flights
Fastest flight time
2h 30m
Cheapest price
$80
Atlanta to Chicago Flights
Fastest flight time
1h 59m
Cheapest price
$81
Dallas to Chicago Flights
Fastest flight time
2h 14m
Cheapest price
$82
Tampa to Chicago Flights
Fastest flight time
2h 47m
Cheapest price
$86
Orlando to Chicago Flights
Fastest flight time
2h 54m
Cheapest price
$95
Oakland to Chicago Flights
Fastest flight time
4h 00m
Cheapest price
$99
Seattle to Chicago Flights
Fastest flight time
3h 50m
Cheapest price
$101
Phoenix to Chicago Flights
Fastest flight time
3h 22m
Cheapest price
$107
Minneapolis to Chicago Flights
Fastest flight time
1h 31m
Cheapest price
$107
Philadelphia to Chicago Flights
Fastest flight time
2h 11m
Cheapest price
$120
New York to Chicago Flights
Fastest flight time
2h 42m
Cheapest price
$129
San Francisco to Chicago Flights
Fastest flight time
3h 57m
Cheapest price
$138
Washington to Chicago Flights
Fastest flight time
2h 03m
Cheapest price
$167
Mexico City to Chicago Flights
Fastest flight time
3h 53m
Cheapest price
$170
Ontario to Chicago Flights
Fastest flight time
3h 49m
Cheapest price
$171
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