Cheap flights to Chicago from New York City

Flights to Chicago from New York City

Price	To/From	Dates	Supplier
1 2 Next
Save up to 50%	Summer Savings Still need to plan your summer travel? Book now and save up to 50 percent on popular vacations, plus get an extra 10 percent instant savings on almost all hotel stays. Date posted: 09 May 2008		Orbitz Book online
$296 RT(excl. tax)	From: New York City, NY (LGA) To: Chicago, IL (ORD)	Travel valid from: 22 May 2008 Travel valid until: 14 Jun 2008 Deal Details	American Airlines Book online
$150 RT(incl. taxes)	From: New York City, NY (LGA) To: Chicago, IL (MDW) Travel valid from: 20 May 2008 Travel valid until: 04 Jun 2008 Deal Details Save $10 instantly. CheapOair. The Only Way to Go		CheapOAir.com Book online
$223 RT(incl. taxes)	From: New York City, NY (LGA) To: Chicago, IL (ORD) Depart: 04 Jun 2008 Return: 11 Jun 2008 Deal Details Save Big. ORBITZ. A Step Ahead.		Orbitz Book online
$182 RT(excl. tax)	From: New York City, NY (LGA) To: Chicago, IL (CHI)	Travel valid from: 11 May 2008 Travel valid until: 10 Apr 2009 Deal Details	CheapAir.com Book online
$199 RT(incl. taxes)	From: New York City, NY (LGA) To: Chicago, IL (ORD) Travel valid from: 29 May 2008 Travel valid until: 02 Jun 2008 Deal Details Save up to 50% off last minute fares!		Hotwire Book online
$179 RT(excl. tax)	From: New York City, NY (NYC) To: Chicago, IL (CHI) Travel valid from: 02 Jun 2008 Travel valid until: 31 Aug 2008 Deal Details Student Airfares - Travel more. Spend less		Student Universe Book online
$221 RT(incl. taxes)	From: New York City, NY (LGA) To: Chicago, IL (ORD) Depart: 04 Jun 2008 Return: 11 Jun 2008 Deal Details Cheap air tickets, hotels, travel deals, and more.		CheapTickets Book online
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$160 RT(incl. taxes)	From: New York City, NY (LGA) To: Chicago, IL (MDW) Travel valid from: 05 Jun 2008 Travel valid until: 20 Jun 2008 Deal Details Save $10 instantly. CheapOair. The Only Way to Go		CheapOAir.com Book online
$162 RT(incl. taxes)	From: New York City, NY (LGA) To: Chicago, IL (MDW) Travel valid from: 21 Jun 2008 Travel valid until: 04 Jul 2008 Deal Details Save $10 instantly. CheapOair. The Only Way to Go		CheapOAir.com Book online
$164 RT(incl. taxes)	From: New York City, NY (LGA) To: Chicago, IL (MDW) Travel valid from: 05 Jul 2008 Travel valid until: 21 Jul 2008 Deal Details Save $10 instantly. CheapOair. The Only Way to Go		CheapOAir.com Book online
$167 RT(incl. taxes)	From: New York City, NY (LGA) To: Chicago, IL (ORD) Travel valid from: 20 May 2008 Travel valid until: 04 Jun 2008 Deal Details Save $10 instantly. CheapOair. The Only Way to Go		CheapOAir.com Book online
$182 RT(excl. tax)	From: New York City, NY (LGA) To: Chicago, IL (ORD)	Travel valid from: 11 May 2008 Travel valid until: 10 Apr 2009 Deal Details	CheapAir.com Book online
$199 RT(incl. taxes)	From: New York City, NY (LGA) To: Chicago, IL (MDW) Travel valid from: 29 May 2008 Travel valid until: 30 May 2008 Deal Details Save up to 50% off last minute fares!		Hotwire Book online
$199 RT(incl. taxes)	From: New York City, NY (LGA) To: Chicago, IL (MDW) Travel valid from: 01 Jun 2008 Travel valid until: 03 Jun 2008 Deal Details Save up to 50% off last minute fares!		Hotwire Book online
$199 RT(incl. taxes)	From: New York City, NY (LGA) To: Chicago, IL (MDW) Travel valid from: 03 Jun 2008 Travel valid until: 04 Jun 2008 Deal Details Save up to 50% off last minute fares!		Hotwire Book online
$204 RT(incl. taxes)	From: New York City, NY (LGA) To: Chicago, IL (ORD) Travel valid from: 21 May 2008 Travel valid until: 02 Jun 2008 Deal Details Save up to 50% off last minute fares!		Hotwire Book online
$204 RT(incl. taxes)	From: New York City, NY (LGA) To: Chicago, IL (MDW) Travel valid from: 12 Jul 2008 Travel valid until: 16 Jul 2008 Deal Details Save up to 50% off last minute fares!		Hotwire Book online
$228 RT(incl. taxes)	From: New York City, NY (LGA) To: Chicago, IL (MDW) Depart: 04 Jun 2008 Return: 11 Jun 2008 Deal Details Cheap air tickets, hotels, travel deals, and more.		CheapTickets Book online
$230 RT(incl. taxes)	From: New York City, NY (LGA) To: Chicago, IL (MDW) Depart: 04 Jun 2008 Return: 11 Jun 2008 Deal Details Save Big. ORBITZ. A Step Ahead.		Orbitz Book online
$239 RT(incl. taxes)	From: New York City, NY (JFK) To: Chicago, IL (ORD) Travel valid from: 02 Aug 2008 Travel valid until: 07 Aug 2008 Deal Details Save up to 50% off last minute fares!		Hotwire Book online
$244 RT(incl. taxes)	From: New York City, NY (JFK) To: Chicago, IL (ORD) Travel valid from: 17 May 2008 Travel valid until: 31 May 2008 Deal Details Save up to 50% off last minute fares!		Hotwire Book online
$244 RT(incl. taxes)	From: New York City, NY (JFK) To: Chicago, IL (ORD) Travel valid from: 27 May 2008 Travel valid until: 10 Jun 2008 Deal Details Save up to 50% off last minute fares!		Hotwire Book online
$244 RT(incl. taxes)	From: New York City, NY (JFK) To: Chicago, IL (MDW) Travel valid from: 30 May 2008 Travel valid until: 08 Jun 2008 Deal Details Save up to 50% off last minute fares!		Hotwire Book online
$244 RT(incl. taxes)	From: New York City, NY (JFK) To: Chicago, IL (MDW) Travel valid from: 31 May 2008 Travel valid until: 09 Aug 2008 Deal Details Save up to 50% off last minute fares!		Hotwire Book online
$249 RT(incl. taxes)	From: New York City, NY (JFK) To: Chicago, IL (ORD) Depart: 27 May 2008 Return: 28 May 2008 Deal Details Other dates & prices offered		Kayak Book online
$250 RT(incl. taxes)	From: New York City, NY (NYC) To: Chicago, IL (CHI) Depart: 04 Jul 2008 Return: 08 Jul 2008 Deal Details Other dates & prices offered		Kayak Book online
$250 RT(incl. taxes)	From: New York City, NY (NYC) To: Chicago, IL (CHI) Depart: 18 Jul 2008 Return: 24 Jul 2008 Deal Details Other dates & prices offered		Kayak Book online
$250 RT(incl. taxes)	From: New York City, NY (NYC) To: Chicago, IL (MDW) Depart: 05 Aug 2008 Return: 10 Aug 2008 Deal Details Other dates & prices offered		Kayak Book online
$250 RT(incl. taxes)	From: New York City, NY (NYC) To: Chicago, IL (CHI) Depart: 11 Aug 2008 Return: 13 Aug 2008 Deal Details Other dates & prices offered		Kayak Book online
$265 RT(incl. taxes)	From: New York City, NY (LGA) To: Chicago, IL (MDW) Depart: 04 Jun 2008 Return: 11 Jun 2008 Deal Details Cheap air tickets, hotels, travel deals, and more.		CheapTickets Book online
$266 RT(incl. taxes)	From: New York City, NY (LGA) To: Chicago, IL (MDW) Depart: 04 Jun 2008 Return: 11 Jun 2008 Deal Details Save Big. ORBITZ. A Step Ahead.		Orbitz Book online
$266 RT(incl. taxes)	From: New York City, NY (LGA) To: Chicago, IL (ORD) Depart: 04 Jun 2008 Return: 11 Jun 2008 Deal Details Save Big. ORBITZ. A Step Ahead.		Orbitz Book online
$266 RT(incl. taxes)	From: New York City, NY (LGA) To: Chicago, IL (ORD) Depart: 25 Jul 2008 Return: 27 Jul 2008 Deal Details Other dates & prices offered		Kayak Book online
$267 RT(incl. taxes)	From: New York City, NY (NYC) To: Chicago, IL (ORD) Depart: 11 Jul 2008 Return: 13 Jul 2008 Deal Details Other dates & prices offered		Kayak Book online
$267 RT(incl. taxes)	From: New York City, NY (LGA) To: Chicago, IL (ORD) Depart: 18 Jul 2008 Return: 20 Jul 2008 Deal Details Other dates & prices offered		Kayak Book online
$267 RT(incl. taxes)	From: New York City, NY (LGA) To: Chicago, IL (ORD) Depart: 19 Jul 2008 Return: 20 Jul 2008 Deal Details Other dates & prices offered		Kayak Book online
$267 RT(incl. taxes)	From: New York City, NY (NYC) To: Chicago, IL (ORD) Depart: 21 Aug 2008 Return: 24 Aug 2008 Deal Details Other dates & prices offered		Kayak Book online
$270 RT(incl. taxes)	From: New York City, NY (LGA) To: Chicago, IL (ORD) Depart: 04 Jun 2008 Return: 11 Jun 2008 Deal Details Cheap air tickets, hotels, travel deals, and more.		CheapTickets Book online
$275 RT(incl. taxes)	From: New York City, NY (NYC) To: Chicago, IL (MDW) Depart: 27 May 2008 Return: 28 May 2008 Deal Details Other dates & prices offered		Kayak Book online
$279 RT(incl. taxes)	From: New York City, NY (JFK) To: Chicago, IL (ORD) Depart: 25 May 2008 Return: 01 Jun 2008 Deal Details Other dates & prices offered		Kayak Book online
$279 RT(incl. taxes)	From: New York City, NY (LGA) To: Chicago, IL (CHI) Depart: 07 Jun 2008 Return: 08 Jun 2008 Deal Details Other dates & prices offered		Kayak Book online
$279 RT(incl. taxes)	From: New York City, NY (LGA) To: Chicago, IL (CHI) Depart: 10 Jun 2008 Return: 20 Jun 2008 Deal Details Other dates & prices offered		Kayak Book online
$279 RT(incl. taxes)	From: New York City, NY (LGA) To: Chicago, IL (CHI) Depart: 13 Jun 2008 Return: 16 Jun 2008 Deal Details Other dates & prices offered		Kayak Book online
$295 RT(incl. taxes)	From: New York City, NY (JFK) To: Chicago, IL (ORD) Depart: 04 Jun 2008 Return: 11 Jun 2008 Deal Details Cheap air tickets, hotels, travel deals, and more.		CheapTickets Book online
$295 RT(incl. taxes)	From: New York City, NY (JFK) To: Chicago, IL (CHI) Depart: 31 Jul 2008 Return: 04 Aug 2008 Deal Details Other dates & prices offered		Kayak Book online
$296 RT(incl. taxes)	From: New York City, NY (JFK) To: Chicago, IL (ORD) Depart: 04 Jun 2008 Return: 11 Jun 2008 Deal Details Save Big. ORBITZ. A Step Ahead.		Orbitz Book online
$304 RT(incl. taxes)	From: New York City, NY (JFK) To: Chicago, IL (CHI) Depart: 20 May 2008 Return: 23 May 2008 Deal Details Other dates & prices offered		Kayak Book online
$320 RT(incl. taxes)	From: New York City, NY (NYC) To: Chicago, IL (MDW) Depart: 17 May 2008 Return: 18 May 2008 Deal Details Other dates & prices offered		Kayak Book online
$325 RT(incl. taxes)	From: New York City, NY (JFK) To: Chicago, IL (MDW) Depart: 04 Jun 2008 Return: 11 Jun 2008 Deal Details Cheap air tickets, hotels, travel deals, and more.		CheapTickets Book online
$326 RT(incl. taxes)	From: New York City, NY (JFK) To: Chicago, IL (MDW) Depart: 04 Jun 2008 Return: 11 Jun 2008 Deal Details Save Big. ORBITZ. A Step Ahead.		Orbitz Book online
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Save up to 60%	4 Star Hotels at 2 Star Prices! Hotels for less with low Hotwire Hot-Rates!		Hotwire Book online

Business Deals

$1,500 RT(excl. tax)	From: New York City, NY (NYC) To: Chicago, IL (CHI) Travel valid from: 11 May 2008 Travel valid until: 10 Apr 2009 Deal Details Major Airline!		CheapAir.com Book online
$1,500 RT(excl. tax)	From: New York City, NY (LGA) To: Chicago, IL (ORD) Travel valid from: 11 May 2008 Travel valid until: 10 Apr 2009 Deal Details Major Airline!		CheapAir.com Book online

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Departure airports

New York City

Destination airports

Chicago

Fact Finder

Avg. Flight Duration2 hr 30 mins

Flight guide to Chicago

Overview of Chicago

As Frank Sinatra crooned, “Chicago is my kind of town,” and many tourists agree. Book a flight to Chicago and shop the Miracle Mile, step back in time at the National History Museum, tour the artist’s lofts in the heart of the city, and enjoy some cool...

Useful Links

Useful links for Chicago

Frommer's guide: The lowdown on Chicago
Fodor’s guide: Get the most out of Chicago
Map: Map of Chicago
Weather: Is it sunny?
Events calendar: What's on when in Chicago

Travel Tips

Read expert tips on getting the most out of travel

Getting Bumped: When airlines overbook, you might lose your seat
Booking Flights by Phone: Best practice for using your phone when purchasing airline tickets
Fat-Finger Fares: The ultimate cheap airline tickets

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