Escape Flights - Chicago/Milwaukee
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chi.escape.flights
Escape Flights - Chicago/Milwaukee
@chi.escape.flights
92 followers 7 following 310 posts
Escape Flights is a blog about airfare deals that are departing out of Chicago/Milwaukee.

Want a notification when flights from ORD, MDW, or MKE go on sale? Give us a follow!

Link: https://escape.flights/flights-from-chicago/
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Cheap Flights: Chicago to/from Lihue-Kauai, Hawaii $336-$348 round-trip [January-March] - American Airlines

escape.flights?p=64262

#Airfare #Flights #Travel #EscapeFlights #Chicago
Cheap Flights: Chicago to/from Lihue-Kauai, Hawaii $336-$348 round-trip [January-March] – American Airlines
American Airlines has round-trip flights from Chicago (ORD) to Lihue-Kauai, Hawaii (LIH) for $336-$348 with a connection. Flights January to March. No weekend departures. Origin/Destination reversible...
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January 14, 2026 at 1:12 AM
chi.escape.flights
Cheap Flights: Chicago to Helsinki $366-$408 round-trip [January-May] - Icelandair

escape.flights?p=64214

#Airfare #Flights #Travel #EscapeFlights #Chicago
Cheap Flights: Chicago to Helsinki $366-$408 round-trip [January-May] – Icelandair
Icelandair has round-trip flights from Chicago (ORD) to Helsinki (HEL) for $366-$408 with a connection. Flights January to May. Some small OTAs on Skyscanner have this for as low as…
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January 12, 2026 at 5:40 PM
chi.escape.flights
Cheap Flights: Chicago to Santiago, Chile $573-$597 round-trip [January-May] - Delta / LATAM / American Airlines / United

escape.flights?p=64179

#Airfare #Flights #Travel #EscapeFlights #Chicago
Cheap Flights: Chicago to Santiago, Chile $573-$597 round-trip [January-May] – Delta / LATAM / American Airlines / United
Delta, LATAM, American Airlines, United and various other airlines have round-trip flights from Chicago (ORD/MDW) to Santiago, Chile (SCL) for $573-$597 with a connection. Flights January to May.
escape.flights
January 8, 2026 at 8:57 PM
chi.escape.flights
Nonstop Flights: Chicago to/from Portland, Oregon $149-$164 round-trip [January-May] - American Airlines / United

escape.flights?p=64176

#Airfare #Flights #Travel #EscapeFlights #Chicago
Nonstop Flights: Chicago to/from Portland, Oregon $149-$164 round-trip [January-May] – American Airlines / United
American Airlines and United have round-trip flights from Chicago (ORD) to Portland, Oregon (PDX) for $149-$164, NONSTOP. Flights January to May. Weekends available. Origin/Destination reversible.
escape.flights
January 8, 2026 at 8:35 PM
chi.escape.flights
Cheap Flights: Chicago to Paris $431-$467 round-trip [January-April] - Icelandair

escape.flights?p=64154

#Airfare #Flights #Travel #EscapeFlights #Chicago
Cheap Flights: Chicago to Paris $431-$467 round-trip [January-April] – Icelandair
Icelandair has round-trip flights from Chicago (ORD) to Paris (CDG) for $431-$467 with a connection. Flights January to April. Some small OTAs on Skyscanner have this for as low as…
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January 7, 2026 at 9:54 PM
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Nonstop Flights: Chicago to/from New York/Newark, Kansas City, Seattle, Dallas, or Austin $109-$145 round-trip [January-February] (use code: GO26) - Southwest / United / American Airlines / jetBlue

escape.flights?p=64114

#Airfare #Flights #Travel #EscapeFlights #Chicago
Nonstop Flights: Chicago to/from New York/Newark, Kansas City, Seattle, Dallas, or Austin $109-$145 round-trip [January-February] (use code: GO26) – Southwest / United / American Airlines / jetBlue
Southwest, United, jetBlue, and American Airlines have round-trip flights from Chicago (MDW/ORD) to New York/Newark, Kansas City, Seattle, Dallas, or Austin (LGA/EWR, MCI, SEA, DFW, AUS) for $109-$145...
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January 6, 2026 at 7:11 PM
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European Airfare Sale: Chicago and Milwaukee to/from various European destinations $385-$650 r/t [varies: Jan-May, Sep-Nov] – Oneworld / Aer Lingus / Icelandair / SAS / SkyTeam

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#Airfare #Flights #Travel #EscapeFlights
European Airfare Sale: to/from various European destinations $310-$650 r/t [varies: Jan-May, Sep-Nov] – Oneworld / Aer Lingus / Icelandair / SAS / SkyTeam
Oneworld, SAS, Aer Lingus, and Icelandair have round-trip flights to various destinations in Europe at a discount today for $310-$650, mostly with a connection. Dates vary, use the linked calendar.…
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January 5, 2026 at 11:30 PM
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Cheap Flights: Chicago to/from Honolulu, Maui, or Kailua-Kona $339-$371 round-trip [January-March] - American Airlines

escape.flights?p=64073

#Airfare #Flights #Travel #EscapeFlights #Chicago
Cheap Flights: Chicago to/from Honolulu, Maui, or Kailua-Kona $339-$371 round-trip [January-March] – American Airlines
American Airlines has round-trip flights from Chicago (ORD) to Honolulu, Maui, or Kailua-Kona (HNL, OGG, KOA) for $339-$371 . Flights January to March. Departures on Monday, Tuesday, Wednesday, and Su...
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January 5, 2026 at 5:21 PM
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Cheap Flights: Chicago to Honolulu or Lihue-Kauai, Hawaii $336-$361 round-trip [January-March] - American Airlines

escape.flights?p=64048

#Airfare #Flights #Travel #EscapeFlights #Chicago
Cheap Flights: Chicago to Honolulu or Lihue-Kauai, Hawaii $336-$361 round-trip [January-March] – American Airlines
American Airlines has round-trip flights from Chicago (ORD) to Honolulu or Lihue-Kauai, Hawaii (HNL, OGG) for $336-$361. Flights January to March. No weekend departures. Honolulu fare is Nonstop, Lihu...
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January 2, 2026 at 7:41 PM
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Cheap Flights: Chicago to/from San Juan, Puerto Rico $151-$160 round-trip [February-May] - JetBlue

escape.flights?p=64044

#Airfare #Flights #Travel #EscapeFlights #Chicago
Cheap Flights: Chicago to/from San Juan, Puerto Rico $151-$160 round-trip [February-May] – JetBlue
JetBlue has round-trip flights from Chicago (ORD) to San Juan, Puerto Rico (SJU) for $151-$160 with a connection. Flights February to May. Origin/Destination reversible. This is about $60 cheaper than...
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January 2, 2026 at 7:26 PM
chi.escape.flights
Cheap Flights: Chicago to Oslo, Norway $366-$399 round-trip [Feb-Apr, Oct-Nov] (No Thanksgiving) - Scandinavian Airlines

escape.flights?p=64041

#Airfare #Flights #Travel #EscapeFlights #Chicago
Cheap Flights: Chicago to Oslo, Norway $366-$399 round-trip [Feb-Apr, Oct-Nov] (No Thanksgiving) – Scandinavian Airlines
Scandinavian Airlines has round-trip flights from Chicago (ORD) to Oslo (OSL) for $366-$399 with a connection. Flights February, March, April, October, and November. No Thanksgiving dates. Some small ...
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January 2, 2026 at 6:51 PM
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Cheap Flights: Chicago to/from Honolulu $318-$379 round-trip [January-March] (Use code: THANKYOU20) - Hawaiian / Alaska Airlines

escape.flights?p=64005

#Airfare #Flights #Travel #EscapeFlights #Chicago
Cheap Flights: Chicago to/from Honolulu $318-$379 round-trip [January-March] (Use code: THANKYOU20) – Hawaiian / Alaska Airlines
Hawaiian and Alaska Airlines have code-share round-trip flights from Chicago (ORD) to Honolulu (HNL) for $318-$379 with a connection. Flights January to March. No weekend departures. Origin/Destinatio...
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December 31, 2025 at 4:20 PM
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Cheap Flights: Chicago to/from Maui-Kahului, Hawaii $320-$392 round-trip [February-March] (Use code: THANKYOU20)- Hawaiian / Alaska Airlines

escape.flights?p=63993

#Airfare #Flights #Travel #EscapeFlights #Chicago
Cheap Flights: Chicago to/from Maui-Kahului, Hawaii $320-$392 round-trip [February-March] (Use code: THANKYOU20)- Hawaiian / Alaska Airlines
Hawaiian and Alaska Airlines have code-share round-trip flights from Chicago (ORD) to Maui-Kahului, Hawaii (OGG) for $320-$392 with a connection. Flights February to March. No weekend departures. Orig...
escape.flights
December 31, 2025 at 4:40 AM
chi.escape.flights
Nonstop Flights: Chicago to/from San Juan, Puerto Rico $216 round-trip [January-March] - United / American Airlines

escape.flights?p=63959

#Airfare #Flights #Travel #EscapeFlights #chicago
Nonstop Flights: Chicago to/from San Juan, Puerto Rico $216 round-trip [January-March] – United / American Airlines
United and American Airlines have round-trip flights from Chicago (ORD) to San Juan, Puerto Rico (SJU) for $216, NONSTOP. Flights January to March. Departures on Monday, Tuesday, Wednesday, and Sunday...
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December 29, 2025 at 7:33 PM
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Nonstop Flights: Chicago to/from Boston or New York $97-$127 round-trip [January-February] - JetBlue / United

escape.flights?p=63946

#Airfare #Flights #Travel #EscapeFlights #Chicago
Nonstop Flights: Chicago to/from Boston or New York $97-$127 round-trip [January-February] – JetBlue / United
JetBlue has round-trip flights from Chicago (ORD) to Boston or New York (BOS, JFK) for $97-$127, NONSTOP. Flights January to February. A few weekends available. Origin/Destination reversible.
escape.flights
December 26, 2025 at 9:27 PM
chi.escape.flights
Cheap Flights: Chicago to Amsterdam or Manchester $440-$523 round-trip [January-March] - Icelandair / Skyscanner

escape.flights?p=63912

#Airfare #Flights #Travel #EscapeFlights #Chicago
Cheap Flights: Chicago to Amsterdam or Manchester $440-$523 round-trip [January-March] – Icelandair / Skyscanner
Icelandair has round-trip flights from Chicago (ORD) to Amsterdam or Manchester (AMS, MAN) for $440-$523 with a connection. Flights January to March. Some small OTAs on Skyscanner have this for…
escape.flights
December 23, 2025 at 6:05 PM
chi.escape.flights
Nonstop Flights: Chicago to/from Honolulu, Hawaii $362-$379 round-trip [January-March] - American Airlines

escape.flights?p=63858

#Airfare #Flights #Travel #EscapeFlights #Chicago
Nonstop Flights: Chicago to/from Honolulu, Hawaii $362-$379 round-trip [January-March] – American Airlines
American Airlines has round-trip flights from Chicago (ORD) to Honolulu (HNL) for $362-$379, NONSTOP. Flights January to March. Departures on Monday, Tuesday, Thursday, and Sunday. Origin/Destination ...
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December 18, 2025 at 10:31 PM
chi.escape.flights
Nonstop Flights: Chicago to/from Punta Cana, Dominican Republic $216-$238 round-trip [January-May] - Arajet

escape.flights?p=63837

#Airfare #Flights #Travel #EscapeFlights #Chicago
Nonstop Flights: Chicago to/from Punta Cana, Dominican Republic $216-$238 round-trip [January-May] – Arajet
Arajet has round-trip flights from Chicago (ORD) to Punta Cana, Dominican Republic (PUJ) for $216-$238, NONSTOP. Flights January to May. Departures on Monday, Wednesday, and Saturday. Origin/Destinati...
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December 18, 2025 at 6:00 PM
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Cheap Flights: Chicago to/from Belize City $366 round-trip [December-March] (No Christmas) - American Airlines

escape.flights?p=63693

#Airfare #Flights #Travel #EscapeFlights #Chicago
Cheap Flights: Chicago to/from Belize City $366 round-trip [December-March] (No Christmas) – American Airlines
American Airlines has round-trip flights from Chicago (ORD) to Belize City (BZE) for $366 with a connection. Flights December to March. Departures on Monday, Tuesday, Wednesday, and Sunday. Origin/Des...
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December 9, 2025 at 8:24 PM
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Nonstop Flights: Chicago to San Jose, Costa Rica $343 round-trip [December-February] (No Christmas) - American Airlines

escape.flights?p=63671

#Airfare #Flights #Travel #EscapeFlights #Chicago
Nonstop Flights: Chicago to San Jose, Costa Rica $343 round-trip [December-February] (No Christmas) – American Airlines
American Airlines has round-trip flights from Chicago (ORD) to San Jose, Costa Rica (SJO) for $343, NONSTOP. Flights December to February. Departures on Monday, Tuesday, Wednesday, and Sunday. No Chri...
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December 6, 2025 at 5:48 PM
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Nonstop Flights: Chicago to Vail, Colorado $211-$237 round-trip [January-February] - United

escape.flights?p=63626

#Airfare #Flights #Travel #EscapeFlights #Chicago
Nonstop Flights: Chicago to Vail, Colorado $211-$237 round-trip [January-February] – United
United has round-trip flights from Chicago (ORD) to Vail, Colorado (EGE) for $211-$237, NONSTOP. Flights January to February. Very few weekends available.
escape.flights
December 4, 2025 at 5:32 PM
chi.escape.flights
Nonstop Flights: Chicago to/from New York $91-$97 r/t [January-March] - United / American Airlines / JetBlue

escape.flights?p=63592

#Airfare #Flights #Travel #EscapeFlights #Chicago
Nonstop Flights: Chicago to/from New York $91-$97 r/t [January-March] – United / American Airlines / JetBlue
United, American Airlines, and JetBlue have competing round-trip fare sales from Chicago (ORD) to New York (LGA/JFK) priced at $91-$97, NONSTOP. Flights January to March. Departures on Monday, Tuesday...
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December 2, 2025 at 8:38 PM
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Cheap Flights: Chicago to/from Kailua-Kona, Hawaii $282-$319 r/t [January-May] - Southwest

escape.flights?p=63561

#Airfare #Flights #Travel #EscapeFlights #Chicago
Cheap Flights: Chicago to/from Kailua-Kona, Hawaii $282-$319 r/t [January-May] – Southwest
Southwest has round-trip flights from Chicago (MDW) to Kailua-Kona, Hawaii (KOA) for $282-$319 with a connection. Flights January to May. Departures on Monday, Tuesday, Wednesday, and Sunday. Origin/D...
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December 2, 2025 at 4:45 PM
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Cheap Flights: Chicago to/from Honolulu $284-$295 r/t [January-February] (Has a 5-hour connection in LAX) - United

escape.flights?p=63536

#Airfare #Flights #Travel #EscapeFlights #Chicago
Cheap Flights: Chicago to/from Honolulu $284-$295 r/t [January-February] (Has a 5-hour connection in LAX) – United
United has round-trip flights from Chicago (ORD) to Honolulu (HNL) for $284-$295 with a connection. Flights January to February. Departures on Tuesday and Wednesday. Origin/Destination reversible. Dow...
escape.flights
December 1, 2025 at 11:25 PM
Reposted by Escape Flights - Chicago/Milwaukee
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Domestic Airfare Sale: to/from various destinations in the USA $63-$199 r/t (New York, Chicago, Seattle, Portland, Denver Phoenix, Atlanta, Las Vegas, Los Angeles, Miami, + more) [mostly Jan-Feb] – Southwest / United / American / Delta

Big domestic sale.

escape.flights?p=63523
Domestic Airfare Sale: to/from various destinations in the USA $63-$199 r/t (New York, Los Angeles, Seattle, Miami, + more) [mostly Jan-Feb] – Southwest / United / American / Delta
Most major domestic airlines have posted a lot of discounted round-trip flights to various destinations in the USA at a discount today for $63-$199, Nonstop or with a connection. Dates…
escape.flights
December 1, 2025 at 4:48 PM