Fly Between Chicago And Baltimore, Los Angeles, Miami, Orlando, NYC, Phoenix, And More On American Or United From $40 Each Way!

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Bookable on Priceline. Tickets purchased from Priceline today are refundable until 11:29pm tomorrow. Please see this post for directions on how to cancel these tickets.

-Also Bookable on Orbitz. Orbitz tickets are refundable until 11pm ET tomorrow.

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-Limited seats are available on each date and dates listed below will sell out! Please post a comment with which dates and route didn’t work for you and I will update the post.

Always search one-way for 1 seat and then work your way up to the number of seats you need in order to book as many seats on sale as you can. Searching round-trip may result in higher prices.

-All flight dates listed below are nonstop.

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Chicago-Baltimore $40-$48 dates in black, $58 dates in red:
January 12, 19, 20, 21, 23, 25, 26, 27, 28, 30
February 1, 2, 3, 4, 6, 8, 9, 10, 13, 16, 17, 23, 24
March 1, 2, 8, 15, 22, 23, 30
April 5, 6

Baltimore-Chicago $40-$48 dates in black, $58 dates in red:
January 12, 20, 23, 26, 27, 30
February 2, 3, 9, 10, 23
March 1, 8, 15, 16, 23, 30
April 5, 6

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Chicago-Boston $48 dates:
January 19, 20, 23, 26, 27, 30
February 2, 3, 6, 9, 10, 13, 16, 17, 23, 24
March 1, 2, 5, 8, 9, 15, 16, 22, 23, 26, 29, 30
April 2, 5, 6, 9, 12, 13, 19, 20, 26, 27
May 3, 4

Boston-Chicago $48 dates:
January 19, 20, 23, 26, 27, 30
February 2, 3, 6, 9, 10, 23, 24, 27
March 1, 2, 8, 9, 12, 15, 16, 19, 22, 23, 26, 29, 30
April 5, 6, 12, 13, 20, 23, 26, 27, 30
May 3, 4, 7, 10, 11, 14, 17, 18, 21, 24, 25
June 1, 7, 8, 14, 15, 21, 22, 28
July 5, 12

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Chicago-Dallas $40-$58 dates:
January 11, 12, 13, 14, 16, 18, 19, 20, 21, 23, 25, 26, 27, 28, 30
February 1, 2, 3, 6, 8, 9, 10, 16, 17, 20, 23, 24, 27, 29
March 1, 2, 3, 5, 7, 8, 9, 12, 14, 15, 16, 22, 23, 24, 26, 29, 30
April 2, 4, 5, 6

Dallas-Chicago $40-$58 dates:
January 11, 12, 13, 14, 16, 18, 19, 20, 21, 23, 25, 26, 27, 28, 30
February 1, 2, 3, 6, 9, 10, 11, 13, 15, 16, 17, 20, 23, 24, 25, 27
March 1, 2, 3, 7, 8, 9, 14, 15, 16, 17, 19, 22, 23, 29, 30
April 5, 6

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Chicago-Denver $40-$48 dates:
January 19, 20, 23, 26
February 2, 16

Denver-Chicago $40-$58 dates:
January 11, 12, 13, 14, 15, 16, 17, 20, 21, 22, 23, 25, 26, 27, 28, 29, 30, 31
February 1, 2, 3, 4, 5, 7, 10, 11, 17
March 2, 8, 9, 15, 16, 23, 30
April 5, 6

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Chicago-Fort Lauderdale $53-$63 dates:
January 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 24, 25, 26, 27, 31
February 1, 2, 7, 8, 14, 15, 16, 21, 22, 23, 28, 29
March 1, 2, 6, 7, 8, 9, 14, 15, 21, 22, 29
April 4, 5, 6, 11, 12, 13

Fort Lauderdale-Chicago $53-$63 dates:
January 12, 13, 20, 21, 22, 26, 27, 28, 29
February 2, 3, 4, 5, 6, 9, 10, 11, 12, 13, 17, 18, 19
March 1, 2, 3, 4, 5, 8, 9, 10, 11, 15, 16, 17, 22, 23, 30
April 6, 7, 13

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Chicago-Fort Myers $53-$58 dates:
January 9, 11, 12, 16, 17, 18, 19, 20, 21, 23, 24, 25, 26, 27, 30, 31
February 1, 2, 7, 8, 14, 15, 16, 21, 22, 23, 27, 28, 29
March 7, 8, 14, 15, 29
April 4, 5, 11, 12

Fort Myers-Chicago $53-$58 dates:
January 9, 11, 12, 13, 14, 5, 16, 17, 21, 22, 23, 26, 28, 29, 30
February 2, 4, 5, 6, 9, 11, 12, 13, 14, 17, 18, 19, 24, 25, 26, 27
March 2, 3, 4, 8, 9, 16

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Chicago-Houston $43 dates:
January 6, 9, 11, 12, 13

Houston-Chicago $43 dates:
January 6, 9, 12, 13, 19
February 2, 3, 4, 5, 9, 10
March 2

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Chicago-LaGuardia $40-$48 dates in black, $58 dates in red:
January 12, 13, 14, 19, 20, 21, 23, 26, 27, 28, 30
February 2, 3, 4, 6, 9, 10, 11, 13, 16, 17, 18, 23, 24, 25
March 1, 2, 3, 8, 9, 10, 15, 16, 17, 22, 23, 24, 28, 29, 30, 31
April 2, 5, 6, 7

LaGuardia-Chicago $40-$48 dates in black, $58 dates in red:
January 11, 12, 13, 14, 18, 19, 20, 21, 23, 25, 26, 27, 28, 30
February 1, 2, 3, 4, 8, 9, 10, 11, 17, 18, 20, 22, 23, 24, 25, 27, 29
March 1, 2, 3, 7, 8, 9, 10, 14, 15, 16, 22, 23, 29, 30
April 4, 5, 6, 7

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Chicago-Las Vegas $63 dates:
January 12, 13, 17, 21, 23, 24, 26, 27, 30, 31
February 22

Las Vegas-Chicago $63 dates:
January 6, 13, 14, 15, 16, 19, 20, 26, 27, 28, 29, 30
February 1, 2, 3, 4, 10, 11, 13, 23, 24

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Chicago-Los Angeles $40 dates in black, $68-$78 dates in red:
January 13, 19, 21, 22, 23, 25, 26, 27, 29, 31
February 2, 3, 9, 23, 24, 29
March 8
April 5, 6, 9, 12, 13

Los Angeles-Chicago $40 dates in black, $68-$78 dates in red:
January 13, 19, 20, 21, 23, 26, 27, 28, 29, 30
February 1, 2, 3, 4, 5, 6, 9, 10, 23, 24, 27
March 1, 2, 4, 7, 8, 9
April 13

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Chicago-Miami $53-$68 dates:
January 6, 9, 11, 12, 16, 18, 19, 20, 22, 23, 24, 25, 26, 27, 30, 31
February 1, 2, 6, 7, 8, 9, 13, 16, 17, 20, 23, 27
March 1

Miami-Chicago $53-$68 dates:
January 21, 22, 23, 26, 27, 28, 29
February 2, 3, 4, 5, 9, 10, 17, 24
March 2

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Chicago-Orlando $48-$58 dates:
January 4, 5, 7, 8, 9, 11, 16, 17, 18, 19, 20, 21, 25, 26, 31
February 1, 2, 8

Orlando-Chicago $48-$58 dates:
January 8, 13, 14, 15, 20, 21, 22, 23, 25, 26, 28, 29
February 2, 3, 4, 5, 6, 9, 10, 11, 17, 18, 19, 25, 26
March 2, 3, 4, 8, 9

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Chicago-Philadelphia $40-$48 dates in black, $58 dates in red:
January 11, 12, 13, 14, 16, 18, 19, 20, 21, 23, 25, 26, 27, 28, 30
February 1, 2, 3, 6, 8, 9, 10, 11, 13, 15, 16, 17, 18, 20, 22, 23, 24, 27, 29
March 1, 2, 3, 5, 7, 8, 9, 10, 12, 14, 15, 16, 17, 19, 21, 22, 23, 24, 26, 28, 29, 30, 31
April 2, 4, 5, 6, 7

Philadelphia-Chicago $40-$48 dates in black, $58 dates in red:
January 11, 12, 13, 14, 16, 18, 19, 20, 21, 23, 26, 27, 28, 30
February 1, 2, 3, 4, 6, 9, 10, 11, 13, 15, 16, 17, 18, 20, 23, 24, 25, 27
March 1, 2, 3, 7, 8, 9, 10, 12, 14, 15, 16, 19, 21, 22, 23, 24, 26, 28, 29, 30, 31
April 2, 4, 5, 6, 7

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Chicago-Phoenix $40-$58 dates:
January 13, 19, 20, 23, 25, 26, 28
March 30
April 5

Phoenix-Chicago $40-$58 dates:
January 11, 14, 16, 20, 21, 23, 26, 27, 28, 30
February 2, 3, 4, 6, 9, 10, 11, 13
March 2, 9

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Chicago-San Diego $40 dates in black, $78 dates in red:
January 16, 17, 18, 19, 21, 22, 23, 24, 25, 26, 29
February 2, 6
March 8

San Diego-Chicago $40 dates in black, $68-$78 dates in red:
January 7, 9, 11, 12, 13, 22, 23, 26, 27
February 2, 3
March 2, 8, 9

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Chicago-San Francisco $63-$68 dates:
January 12, 19, 20, 22, 23, 24, 26, 27, 31
February 14, 28, 29
March 2

San Francisco-Chicago $68 dates:
January 22, 26, 27, 29
February 2, 3, 5, 17, 19, 24
March 1, 2

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Leave a Reply

21 Comments On "Fly Between Chicago And Baltimore, Los Angeles, Miami, Orlando, NYC, Phoenix, And More On American Or United From $40 Each Way!"

All opinions expressed below are user generated and the opinions aren’t provided, reviewed or endorsed by any advertiser or DansDeals.

Yosef_S

ORD-FLL is showing cheaper than $63 for some dates. I’m pulling up $53 for multiple AA flights on 2/2 for example.

Dan

@Yosef_S:
Should have said $53-$63, thanks.

Yosef_S

Np. In taking the time to point that out, I lost the seat I wanted. >:-(

That’s what I get for breaking Rule #1: Book now, talk later!!

Dan

@Yosef_S:
Yup, especially when it’s cancellable until tomorrow night…

Anonymous

Chicago is cold

Anonymous

@Anonymous: +1

FlyFirst

Spirit has some dates LGA-ORD for $35
I wouldn’t recommend anyone flying with them though

Nechama

Any options from MSP?

Tee Ay

No dates NYC to Miami?

Yitzchok

Actually did a search with Spirit directly and round trip between Chicago and Dallas is $68 round-trip while it’s $80 on Priceline

Dan

@Yitzchok:
If you buy those Spirit tickets at the airport they’ll be another $36 less than on their site.
But you’ll pay for everything and heaven forbid if there’s an issue with the plane or weather, far better to book the AA and United deals in this post.

rena

how do I book Chicago-I never used dans deals

Yosef_S

@Dan: That’s OK, I found a diff option that works. For a total of $239 + 7.5K Avios + 10K FreeSpirit miles (which I got for $0 from several of their recent promos) I just booked myself for Midwinter in Miami, a Shabbos in Dallas and a wedding in NY!

Yosef_S

@Anonymous: Yes! Very! Luckily, these options can take us somewhere else!!!

Anonymous

No fares less than $209 ORD-FLL Jan. 14

anonymous

Can’t seem to find anything from LA to Chicago for feb 4th…

Andrew

Nothing available from Chicago to FLL or MIA at that price

ephraim

I tried booking a flight from Ord-LGa Jan 14-18 and it seems as though the pricing increased from $58 each way to 480.

Yaakov

There is now flights available to and from Chicago for $36 each way on sprit

Dan

@Yaakov:
Pay the extra money and fly a better airline.

yitzy

where are the links to go to these flights and buy

wpDiscuz