Cheap Flights to Chicago, Illinois from $152.96

Chicago Flights as Low as $152.96

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Fri, Nov 2 - Wed, Nov 7

BOS

Logan Intl.

to

ORD

O'Hare Intl.

$152.96

roundtrip

just found

Open BOS to ORD flights search result page

Wed, Sep 26 - Wed, Oct 10

LGA

LaGuardia

to

ORD

O'Hare Intl.

$171.39

roundtrip

just found

Open LGA to ORD flights search result page

Sat, Oct 13 - Mon, Oct 15

BWI

Baltimore Washington Intl. Thurgood Marshall

to

ORD

O'Hare Intl.

$178.95

roundtrip

found 1 hour ago

Open BWI to ORD flights search result page

Tue, Oct 9 - Fri, Oct 12

LAX

Los Angeles Intl.

to

ORD

O'Hare Intl.

$187.37

roundtrip

just found

Open LAX to ORD flights search result page

Mon, Oct 1 - Wed, Oct 3

JFK

John F. Kennedy Intl.

to

ORD

O'Hare Intl.

$192.11

roundtrip

just found

Open JFK to ORD flights search result page

Thu, Nov 15 - Thu, Nov 22

EWR

Liberty Intl.

to

ORD

O'Hare Intl.

$245.63

roundtrip

just found

Open EWR to ORD flights search result page

Sat, Oct 20 - Tue, Oct 23

SFO

San Francisco Intl.

to

ORD

O'Hare Intl.

$265.00

roundtrip

just found

Open SFO to ORD flights search result page

Wed, Nov 28 - Sat, Dec 1

DCA

Ronald Reagan Washington National

to

ORD

O'Hare Intl.

$271.59

roundtrip

found 16 hours ago

Open DCA to ORD flights search result page

It's time to fly. What's waiting for you in Chicago?

Perhaps you’re searching cheap flights to Chicago for a much-needed vacation or you simply have to roll in to see the relatives. Either way, we say rock that family reunion. Tell one too many stories at the hotel bar. Traveling for work? Crush it. If you lie back and relax without your cell phone, we won’t tell.

In the end you want to score a great deal and have a fantastic time, right? Flying is a small part of the whole adventure. We get that. Wherever you’re excited to go – or get away from – start this story with Hotwire’s cheap flights to Chicago.

Not sure how to get the best price on plane tickets to Chicago?

We know there are some airline aficionados out there. If you don’t know the industry like the back of your hand, don’t worry. You can make spending less look good with our booking tips.

Search certain days of the week for Chicago flights

For better savings, consider departing on a Wednesday, Thursday or Saturday. Return on a Sunday, Tuesday or Wednesday. International deals are often available when departing Monday through Thursday.

Change up your days for cheaper weekend getaways

Jetting off on Thursday and returning on Sunday is generally less expensive than flying on Friday and returning on Monday.

Stay a Saturday night to play more

Spending the weekend at your destination will generally result in lower airfares. We’re all for that.

Consider alternate airports when searching Chicago flights

Other nearby airports may offer different fares from your current search results. Clicking “Nearby Airports” after your initial search will give a list of the closest options.

See a fare that you like? Pounce!

Coordinate with your travel buddies before searching and you’ll be able to act quickly when it’s time to book. Airline ticket prices often change in minutes. We know you’re combing for the best prices but so is everyone else! If the deal is right, snag it and feel the sweet satisfaction of booking victory.

Fly during the off-peak season

Certain travel destinations have especially high volume during particular seasons. For example, Europe, Hawaii and Alaska are big hits in the summer. Florida, New Orleans and Southern California are the most popular in springtime. Winter is prime for Mexico and the Caribbean, as well as ski and snowboard destinations like the Colorado Rockies. In the autumn, Northern California, the Pacific Northwest and New England draw visitors. Flying during less popular periods can mean extra money in your wallet – yes, please!