Fly from
Budget
£48 - £173
Route
Depart
Return
Price
New York LaGuardiaChicago O'Hare Intl
LGA - ORD
LGAORD
New York LaGuardia
Tue 14/5
Nonstop2h 39m
Chicago O'Hare Intl
Tue 14/5
Nonstop2h 11m
New York LaGuardiaChicago O'Hare Intl
LGA - ORD
LGAORD
New York LaGuardia
Sat 6/4
Nonstop2h 46m
Chicago O'Hare Intl
Tue 30/4
Nonstop2h 15m
New York LaGuardiaChicago O'Hare Intl
LGA - ORD
LGAORD
New York LaGuardia
Mon 13/5
Nonstop2h 39m
Chicago O'Hare Intl
Mon 13/5
Nonstop2h 11m
New York John F Kennedy IntlChicago O'Hare Intl
JFK - ORD
JFKORD
New York John F Kennedy Intl
Wed 8/5
Nonstop2h 56m
Chicago O'Hare Intl
Sat 11/5
Nonstop2h 28m
New York LaGuardiaChicago O'Hare Intl
LGA - ORD
LGAORD
New York LaGuardia
Tue 11/6
Nonstop2h 45m
Chicago O'Hare Intl
Tue 25/6
Nonstop2h 16m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Wed 3/4
Nonstop2h 59m
Chicago O'Hare Intl
Sat 6/4
Nonstop2h 17m
JacksonvilleChicago O'Hare Intl
JAX - ORD
JAXORD
Jacksonville
Sat 20/4
Nonstop2h 43m
Chicago O'Hare Intl
Wed 24/4
Nonstop2h 27m
San FranciscoChicago O'Hare Intl
SFO - ORD
SFOORD
San Francisco
Wed 10/4
Nonstop4h 21m
Chicago O'Hare Intl
Sat 20/4
Nonstop4h 46m
Los AngelesChicago O'Hare Intl
LAX - ORD
LAXORD
Los Angeles
Fri 19/4
1 stop24h 43m
Chicago O'Hare Intl
Fri 26/4
1 stop23h 03m
Currently, January is the cheapest month in which you can book a flight to Chicago (average of £601). Flying to Chicago in July will prove the most costly (average of £782). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.
January
£472
February
£486
March
£478
April
£484
May
£484
June
£594
July
£614
August
£562
September
£527
October
£508
November
£487
December
£496
Peak season:
If you’ve been to New York then why not book cheap flights to Chicago, the nation’s second city? The skyscraper metropolis is a feat of modern architecture, as well as home to what was once the world’s tallest building, Sears Tower. It is not a traditional tourist destination but as the hub of the Midwest, Chicago much to offer as a holiday destination. Featuring world-class art galleries and science museums, huge parks and sandy beaches, it also has a multicultural vibe (thanks to the Poles, the Italians, the Greeks and the Irish among many other groups). Peak tourist season is summer (June to August). This coincides with the festival season with many major events taking place in Chicago parks and neighbourhoods every weekend, in spite of the heat and humidity. Taste of Chicago, an outdoor food festival which showcases the variety of cuisines and local flavours, is in mid-July at the lakefront. If you book flights to Chicago during this popular festival, expect crowds of visitors in the area and a rise in the price of flight tickets. August is host to another popular event – the Chicago Air and Water Show. With its free admission and lakefront location, the show attracts huge numbers of fans of aviation and adventure seekers.
Off season:
Chicago is least busy in January through March making cheap flights to Chicago and hotel deals attainable. However, true to its reputation as the ‘Windy City’, cold temperatures and brisk winds will make you want to stay inside for most of your visit.
CHI Temperature | -5 - 23 °C |
---|
If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).
Savvy travellers are always on the lookout for the cheapest flights to Chicago but one of the biggest challenges for figuring out when to go can be the weather. If you don’t enjoy extreme temperatures, fiercely hot summers and bitterly cold winters, then give these two seasons a miss. April through May or September through October are the most enjoyable and mild months of the year in Chicago. You’ll still get warm weather and the hotel rates are more reasonable.
Overall
Comfort
Crew
Entertainment
Boarding
Food
Reviews
It was a good experience other than a short delay.
Overall
Comfort
Crew
Entertainment
Boarding
Food
Reviews
It was a good experience other than a short delay.
Overall
Comfort
Crew
Entertainment
Boarding
Food
Reviews
It was a good experience other than a short delay.
Overall
Comfort
Crew
Entertainment
Boarding
Food
Reviews
It was a good experience other than a short delay.
Overall
Comfort
Crew
Entertainment
Boarding
Food
Reviews
It was a good experience other than a short delay.
Deals for Chicago flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose to your preference, such as price, airport, cabin class, and plenty of other options.
By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Chicago.
Need flexible booking options for your flight to Chicago ? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.
Yes, Cheapflights has a feature called Price Alerts, which notifies users when flight prices change. Track prices for your flight to Chicago today and book when you’re ready!