Discover the Best Cheap Flight Deals from Chicago

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Latest cheap flight deals departing from Chicago.

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What is a premium fare? Airfare that is greater than 60% off the normal ticket price as well as airfare deals to top destinations such as Hawaii and Alaska.

Flights Options
Departure Airport(s)
Destination Airport(s)

$619

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Nov - Feb 2020
๐Ÿ’ฐ $621

๐Ÿ‡บ๐Ÿ‡ธ Chicago, United States
๐Ÿ‡ฒ๐Ÿ‡พ Telupid, Malaysia

Travel Between: ย November 2019 to February 2020

$273

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Jan - May 2020 / Nov - Nov 2019
๐Ÿ’ฐ $0

๐Ÿ‡บ๐Ÿ‡ธ Chicago, United States
๐Ÿ‡ช๐Ÿ‡ธ Barcelona, Spain

Travel Between: November to November 2019 and January to May 2020

๐Ÿ”ฅ 63% OFF 3 star hotels in Barcelona — $165 $60 per night

$621

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Jan - Feb 2020 / Nov - Dec 2019
๐Ÿ’ฐ $319

๐Ÿ‡บ๐Ÿ‡ธ Chicago, United States
๐Ÿ‡ฎ๐Ÿ‡ฑ Tel Aviv, Israel

Travel Between: November to December 2019 and January to February 2020

๐Ÿ”ฅ 4% OFF 3 star hotels in Tel Aviv — $103 $99 per night

$435

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Sep - Nov 2020
๐Ÿ’ฐ $565

๐Ÿ‡บ๐Ÿ‡ธ Chicago, United States
๐Ÿ‡ฎ๐Ÿ‡ช Dublin, Ireland

Travel Between: There's availability from September through November

๐Ÿ”ฅ 12% OFF 3 star hotels in Dublin — $141 $124 per night

$111

*** - *** 2019
๐Ÿ’ฐ $57 โšก

๐Ÿ‡บ๐Ÿ‡ธ Chicago, United States
๐Ÿ‡บ๐Ÿ‡ธ Myrtle Beach, United States

Travel Between: โšก Upgrade to premium plan to get access to travel dates and more.

$548

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Oct - Feb 2020
๐Ÿ’ฐ $552

๐Ÿ‡บ๐Ÿ‡ธ Chicago, United States
๐Ÿ‡ฐ๐Ÿ‡ผ Kuwait City, Kuwait

Travel Between: ย October 2019 to February 2020

๐Ÿ”ฅ 66% OFF 3 star hotels in Kuwait City — $539 $181 per night

$573

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Nov - Mar 2020
๐Ÿ’ฐ $577

๐Ÿ‡บ๐Ÿ‡ธ Chicago, United States
๐Ÿ‡ฑ๐Ÿ‡ง Beirut, Lebanon

Travel Between: ย November 2019 to March 2020

๐Ÿ”ฅ 56% OFF 3 star hotels in Beirut — $150 $67 per night

$175

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Oct - Dec 2019
๐Ÿ’ฐ $90

๐Ÿ‡บ๐Ÿ‡ธ Chicago, United States
๐Ÿ‡ฉ๐Ÿ‡ด Punta Cana, Dominican Republic

Travel Between: October to December 2019

$189

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๐Ÿ’ฐ $0

๐Ÿ‡บ๐Ÿ‡ธ Chicago, United States
๐Ÿ‡ฒ๐Ÿ‡ฝ Cancun, Mexico

Travel Between:

๐Ÿ”ฅ 3% OFF 3 star hotels in Cancun — $58 $56 per night

$523

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Jan - Mar 2020 / Nov - Nov 2019
๐Ÿ’ฐ $34

๐Ÿ‡บ๐Ÿ‡ธ Chicago, United States
๐Ÿ‡ฌ๐Ÿ‡ช Tbilisi, Georgia

Travel Between: November to November 2019 and January to March 2020

๐Ÿ”ฅ 4% OFF 3 star hotels in Tbilisi — $43 $41 per night

$523

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Jan - Mar 2020 / Nov - Nov 2019
๐Ÿ’ฐ $269

๐Ÿ‡บ๐Ÿ‡ธ Chicago, United States
๐Ÿ‡ป๐Ÿ‡ณ Rach Gia, Vietnam

Travel Between: November to November 2019 and January to March 2020

๐Ÿ”ฅ 64% OFF 3 star hotels in Rach Gia — $118 $43 per night

$491

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Jan - Mar 2020 / Nov - Dec 2019
๐Ÿ’ฐ $252

๐Ÿ‡บ๐Ÿ‡ธ Chicago, United States
๐Ÿ‡ฌ๐Ÿ‡ช Tbilisi, Georgia

Travel Between: November to December 2019 and January to March 2020

๐Ÿ”ฅ 4% OFF 3 star hotels in Tbilisi — $64 $61 per night

$541

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Jan - Apr 2020 / Nov - Nov 2019
๐Ÿ’ฐ $278

๐Ÿ‡บ๐Ÿ‡ธ Chicago, United States
๐Ÿ‡ฒ๐Ÿ‡พ Kuala Lumpur, Malaysia

Travel Between: November to November 2019 and January to April 2020

๐Ÿ”ฅ 64% OFF 3 star hotels in Kuala Lumpur — $146 $53 per night

$237

*** - *** 2020
๐Ÿ’ฐ $163 โšก

๐Ÿ‡บ๐Ÿ‡ธ Chicago, United States
๐Ÿ‡บ๐Ÿ‡ธ San Francisco, United States

Travel Between: โšก Upgrade to premium plan to get access to travel dates and more.

๐Ÿ”ฅ 23% OFF 3 star hotels in San Francisco — $296 $229 per night

$295

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Dec - Mar 2020
๐Ÿ’ฐ $151

๐Ÿ‡บ๐Ÿ‡ธ Chicago, United States
๐Ÿ‡ช๐Ÿ‡ธ Barcelona, Spain

Travel Between: Departures: December 3, January 14, 21, 28, February 4, 11, 18, 25-26, March 3 Returns: December 10, January 10, 14, 17, 21, 24, 28, 31, February 4, 7, 11, 14, 18, 25-26, March 3, 5-6, 10 Allow 7 days between departure and return, will take trial and error.

๐Ÿ”ฅ 63% OFF 3 star hotels in Barcelona — $161 $59 per night

$488

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Jan - Mar 2020 / Nov - Dec 2019
๐Ÿ’ฐ $251

๐Ÿ‡บ๐Ÿ‡ธ Chicago, United States
๐Ÿ‡น๐Ÿ‡ท Istanbul, Turkey

Travel Between: November to December 2019 and January to March 2020

๐Ÿ”ฅ 62% OFF 3 star hotels in Istanbul — $322 $123 per night

$37

*** - *** 2019
๐Ÿ’ฐ $19 โšก

๐Ÿ‡บ๐Ÿ‡ธ Chicago, United States
๐Ÿ‡บ๐Ÿ‡ธ New Orleans, United States

Travel Between: โšก Upgrade to premium plan to get access to travel dates and more.

$492

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Jan - Mar 2020 / Nov - Dec 2019
๐Ÿ’ฐ $253

๐Ÿ‡บ๐Ÿ‡ธ Chicago, United States
๐Ÿ‡ฒ๐Ÿ‡ฆ Casablanca, Morocco

Travel Between: November to December 2019 and January to March 2020

$488

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Nov - Mar 2020
๐Ÿ’ฐ $492

๐Ÿ‡บ๐Ÿ‡ธ Chicago, United States
๐Ÿ‡น๐Ÿ‡ท Istanbul, Turkey

Travel Between: ย November 2019 to March 2020

๐Ÿ”ฅ 62% OFF 3 star hotels in Istanbul — $328 $126 per night

$566

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Jan - Mar 2020 / Oct - Nov 2019
๐Ÿ’ฐ $1

๐Ÿ‡บ๐Ÿ‡ธ Chicago, United States
๐Ÿ‡น๐Ÿ‡ญ Bangkok, Thailand

Travel Between: October to November 2019 and January to March 2020

$483

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Jan - Feb 2020 / Nov - Dec 2019
๐Ÿ’ฐ $248

๐Ÿ‡บ๐Ÿ‡ธ Chicago, United States
๐Ÿ‡ฒ๐Ÿ‡ฆ Marrakech, Morocco

Travel Between: November to December 2019 and January to February 2020

$44

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Sep - Dec 2019
๐Ÿ’ฐ $22

๐Ÿ‡บ๐Ÿ‡ธ Chicago, United States
๐Ÿ‡น๐Ÿ‡จ Cockburn Town, Turks And Caicos Islands

Travel Between: September to December 2019

$44

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Sep - Dec 2019
๐Ÿ’ฐ $22

๐Ÿ‡บ๐Ÿ‡ธ Chicago, United States
๐Ÿ‡จ๐Ÿ‡บ Havana, Cuba

Travel Between: September to December 2019

$44

*** - *** 2019
๐Ÿ’ฐ $22 โšก

๐Ÿ‡บ๐Ÿ‡ธ Chicago, United States
๐Ÿ‡บ๐Ÿ‡ธ Los Angeles, United States

Travel Between: โšก Upgrade to premium plan to get access to travel dates and more.
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