$25 Cheap Direct Flights to Chicago

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Cheap Direct Flight Deals to Chicago

Here are some of the best deals found on KAYAK recently from the most popular airlines for direct round-trip flights to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Discover the best prices for you by selecting your travel dates on KAYAK.

5:55 am - 7:27 amEWR-ORD

2h 32mnonstop

9:08 pm - 12:29 amORD-EWR

2h 21mnonstop

$72Spirit Airlines

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Wed, May 28 - Wed, Jun 4

6:30 pm - 8:07 pmLGA-ORD

2h 37mnonstop

5:51 am - 9:00 amORD-LGA

2h 09mnonstop

$74Spirit Airlines

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Wed, May 28 - Wed, Jun 4

2:40 pm - 5:07 pmDFW-MDW

2h 27mnonstop

8:00 am - 10:29 amMDW-DFW

2h 29mnonstop

$94Frontier

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Tue, Jun 17 - Sat, Jun 21

2:40 pm - 5:07 pmDFW-MDW

2h 27mnonstop

8:05 am - 10:32 amMDW-DFW

2h 27mnonstop

$95Frontier

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Tue, Jun 17 - Sat, Jul 12

2:08 pm - 4:03 pmBOS-ORD

2h 55mnonstop

8:40 pm - 12:20 amORD-BOS

2h 40mnonstop

$118American Airlines

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Sat, Jun 7 - Tue, Jun 10

7:45 am - 9:43 amBOS-ORD

2h 58mnonstop

7:54 pm - 11:21 pmORD-BOS

2h 27mnonstop

$134United Airlines

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Sun, May 25 - Wed, May 28

12:15 pm - 2:12 pmBOS-ORD

2h 57mnonstop

6:25 pm - 9:57 pmORD-BOS

2h 32mnonstop

$135United Airlines

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Sat, May 10 - Sat, May 17

9:00 am - 11:09 amJFK-ORD

3h 09mnonstop

4:44 pm - 8:00 pmORD-JFK

2h 16mnonstop

$138American Airlines

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Tue, May 13 - Wed, May 14

10:35 am - 11:50 amBWI-ORD

2h 15mnonstop

1:50 pm - 4:50 pmORD-BWI

2h 00mnonstop

$168Southwest

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Sat, Jul 5 - Thu, Jul 10

11:55 am - 1:05 pmBWI-ORD

2h 10mnonstop

1:50 pm - 4:50 pmORD-BWI

2h 00mnonstop

$280Southwest

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Fri, Jun 27 - Mon, Jun 30

Useful Info

KAYAK's insights & trends for direct flights to Chicago

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