Escape Flights - Chicago/Milwaukee
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chi.escape.flights
Escape Flights - Chicago/Milwaukee
@chi.escape.flights
110 followers 10 following 440 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 Auckland, New Zealand $886 round-trip [October-April] (No Holidays) - Delta

escape.flights?p=67210

#Airfare #Flights #Travel #EscapeFlights #Chicago
Cheap Flights: Chicago to Auckland, New Zealand $886 round-trip [October-April] (No Holidays) – Delta
Delta has round-trip flights from Chicago (ORD) to Auckland, New Zealand (AKL) for $886 with a connection. Flights October to April. Departures on Monday, Tuesday, Wednesday, and Sunday. Holiday black...
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September 16, 2026 at 8:36 PM
chi.escape.flights
What do you think of Icelandair? Are their fare sales worth tracking?

I think $422 is a pretty good price for Chicago-Rome, round-trip.

Paris and other destinations are also part of their sale. Visit our website for more example dates and details. We don't have a paywall.
September 16, 2026 at 5:25 PM
chi.escape.flights
Cheap Flights: Chicago to Gdansk, Berlin, Rome, or Paris $415-$524 round-trip [dates? read the post] (No Holidays) - Icelandair

escape.flights?p=67198

#Airfare #Flights #Travel #EscapeFlights #Chicago
Cheap Flights: Chicago to Gdansk, Berlin, Rome, or Paris $415-$524 round-trip [dates? read the post] (No Holidays) – Icelandair
Icelandair has round-trip flights from Chicago (ORD) to Gdansk, Berlin, Rome, or Paris (GDN, BER, FCO, CDG) for $415-$524 with a connection. Holiday blackouts. Gdansk: Flights October to February and…
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September 16, 2026 at 5:21 PM
chi.escape.flights
Get it while you can. Some of these have a 4-hour connection but I think that it's worth it at this price.

$113 one-way.
$225 round-trip.

MDW to Honolulu...

Let me know if you want more coverage of these types of airfare deals by leaving a like or a comment.
September 15, 2026 at 10:43 PM
chi.escape.flights
Cheap Flights: Chicago to/from Honolulu $226 round-trip ($113 one-way) [November-December] (No Holidays) - Delta / Southwest

escape.flights?p=67169

#Airfare #Flights #Travel #EscapeFlights #Chicago
Cheap Flights: Chicago to/from Honolulu $226 round-trip ($113 one-way) [November-December] (No Holidays) – Delta / Southwest
[09/15/2026 @ 05:03 PM CT] Deal time-stamp. To book: Use our updated link list. Delta and Southwest have round-trip flights from Chicago (MDW,ORD) to Honolulu (HNL) for $226 with a…
escape.flights
September 15, 2026 at 10:41 PM
chi.escape.flights
$437 - Nonstop, round-trip, Puerto Vallarta Mexico.

Want more coverage of Mexico airfare deals? Leave a comment or a like to let me know.

I don't hide deals behind a paywall.
September 15, 2026 at 3:58 PM
chi.escape.flights
Nonstop Flights: Chicago to Puerto Vallarta $438-$447 round-trip ($200-$208 one-way) [October-March] (No Holidays) - American Airlines / United

escape.flights?p=67137

#Airfare #Flights #Travel #EscapeFlights #Chicago
Nonstop Flights: Chicago to Puerto Vallarta $438-$447 round-trip ($200-$208 one-way) [October-March] (No Holidays) – American Airlines / United
American Airlines and United have round-trip flights from Chicago (ORD) to Puerto Vallarta (PVR) for $438-$447, Nonstop. $200-$208 one-way. Flights October to March. A few weekends available. Holiday ...
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September 15, 2026 at 3:53 PM
chi.escape.flights
Nonstop Flights: Chicago to Montego Bay, Jamaica $358-$366 round-trip ($159 one-way) [October-February] (No Holidays) - United

escape.flights?p=67121

#Airfare #Flights #Travel #EscapeFlights #Chicago
Nonstop Flights: Chicago to Montego Bay, Jamaica $358-$366 round-trip ($159 one-way) [October-February] (No Holidays) – United
United has round-trip flights from Chicago (ORD) to Montego Bay, Jamaica (MBJ) for $358-$366, Nonstop. $159 one-way. Flights October to February. A few weekends available. Holiday blackouts.
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September 15, 2026 at 12:04 AM
chi.escape.flights
Here's a good example of a round-trip flight to Rio de Janeiro for $550 that American Airlines posted today.

Let me know if you want more coverage of Brazilian airfare deals by leaving a comment or a like.

See previous post for more details on date ranges and such.
September 14, 2026 at 11:46 PM
chi.escape.flights
Cheap Flights: Chicago to Rio de Janeiro $551 round-trip [Oct, Feb-May] - American Airlines

escape.flights?p=67118

#Airfare #Flights #Travel #EscapeFlights #Chicago
Cheap Flights: Chicago to Rio de Janeiro $551 round-trip [Oct, Feb-May] – American Airlines
American Airlines has round-trip flights from Chicago (ORD) to Rio de Janeiro (GIG) for $551 with a connection. Flights October and also February to May. No Thursday or Friday departures.
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September 14, 2026 at 11:43 PM
chi.escape.flights
Did you know that Milwaukee often has competitive fare sales to Maui? Let me know if you want more MKE / Hawaii airfare deal coverage.

Here's a round-trip, flight from MKE to Maui(OGG).

$202 one-way.
$404 round-trip.

Flights between October to February.
September 14, 2026 at 9:50 PM
chi.escape.flights
Cheap Flights: Milwaukee to/from Maui/Kahului, Hawaii $404 round-trip ($202 one-way) [October-February] (No Holidays) - American Airlines / United

escape.flights?p=67101

#Airfare #Flights #Travel #EscapeFlights #Milwaukee
Cheap Flights: Milwaukee to/from Maui/Kahului, Hawaii $404 round-trip ($202 one-way) [October-February] (No Holidays) – American Airlines / United
American Airlines and United have round-trip flights from Milwaukee (MKE) to Maui/Kahului, Hawaii (OGG) for $404 with a connection. $202 one-way. Flights October to February. A few weekends available....
escape.flights
September 14, 2026 at 9:46 PM
chi.escape.flights
$230 is a good price for nonstop, round-trip flights to San Francisco, but this fare is worth noting due to the lack of Holiday Blackout dates.

Here's an example for San Francisco with Before Christmas / After Christmas flights.

Want more Holiday airfare coverage? let me know.
September 14, 2026 at 8:13 PM
chi.escape.flights
Nonstop Flights: Chicago to/from San Francisco or Las Vegas $209-$231 round-trip ($105-$116 one-way) [October-February] (Holiday availability) - American Airlines / Southwest / United

escape.flights?p=67087

#Airfare #Flights #Travel #EscapeFlights #Chicago
Nonstop Flights: Chicago to/from San Francisco or Las Vegas $209-$231 round-trip ($105-$116 one-way) [October-February] (Holiday availability) – American Airlines / Southwest / United
American Airlines, Southwest, and United have round-trip flights from Chicago (MDW,ORD) to San Francisco or Las Vegas (SFO, LAS) for $109-$231, Nonstop. $105-$116 one-way. Flights October to February....
escape.flights
September 14, 2026 at 8:08 PM
chi.escape.flights
What do you think of TAP Air Portugal to Barcelona, round-tirp for $505?

Decent deal or nah? Any fans (or detractors) feel free to chime in, but I think this is a pretty good price for the distance.

Help keep this page available for free by leaving a like or a comment.
September 12, 2026 at 4:43 PM
chi.escape.flights
Cheap Flights: Chicago to Barcelona $505-$584 round-trip [October-April] (No Holidays) - Tap Air Portugal

escape.flights?p=67047

#Airfare #Flights #Travel #EscapeFlights #Chicago
Cheap Flights: Chicago to Barcelona $505-$584 round-trip [October-April] (No Holidays) – Tap Air Portugal
Tap Air Portugal has round-trip flights from Chicago (ORD) to Barcelona (BCN) for $505-$584 with a connection. Flights October to April. Weekends available. 7-day minimum stay required. Holiday blacko...
escape.flights
September 12, 2026 at 4:39 PM
chi.escape.flights
Still seeing a lot of European fares on sale today.

Oneworld started their sale two days ago, Skyteam and Star Alliance have matched on some of these routes, bringing the price down a bit more.

I think ORD-ATH (Greece) for $553 round-trip is a really good price.
September 10, 2026 at 2:44 PM
chi.escape.flights
Cheap Flights: Chicago to Athens $552-$579 round-trip [November-March] (No Holidays) - Air Canada / American Airlines / British Airways / Lufthansa / United

escape.flights?p=67000

#Chciago #Athens
Cheap Flights: Chicago to Athens $552-$579 round-trip [November-March] (No Holidays) – Air Canada / American Airlines / British Airways / Lufthansa / United
Air Canada, American Airlines, British Airways, Lufthansa, and United have round-trip flights from Chicago (ORD) to Athens (ATH) for $552-$579 with a connection. Flights November to March. Departures ...
escape.flights
September 10, 2026 at 2:40 PM
chi.escape.flights
European Airfare Sale: to/from various European destinations $389-$720 r/t [dates vary] – Oneworld / Aer Lingus / Icelandair / SAS / SkyTeam

escape.flights?p=66901

#Airfare #Flights #Travel #EscapeFlights
September 8, 2026 at 6:58 PM
chi.escape.flights
I think this is a pretty good price for nonstop, round-trip flights to/from Toronto for Thanksgiving.

There are more dates available, but usually Holiday dates don't participate in these fare sales. In this case, it does..
September 8, 2026 at 4:38 PM
chi.escape.flights
Nonstop Flights: Chicago to/from Toronto $211 round-trip [September-December] (Thanksgiving availability) - Air Canada / United

escape.flights?p=66887

#Airfare #Flights #Travel #EscapeFlights #Chicago
Nonstop Flights: Chicago to/from Toronto $211 round-trip [September-December] (Thanksgiving availability) – Air Canada / United
Air Canada and United have round-trip flights from Chicago (ORD) to Toronto (YYZ) for $211, Nonstop. Flights September to December. Origin/Destination reversible. Thanksgiving dates available.
escape.flights
September 8, 2026 at 4:35 PM
chi.escape.flights
Cheap Flights: Chicago to Zagreb, Croatia, Sofia, Bulgaria, or Belgrade, Serbia $645-$678 round-trip [Oct-Dec, Feb / Oct-Dec, Feb-May / Nov] (No Holidays) - LOT

escape.flights?p=66884

#Airfare #Flights #Travel #EscapeFlights #Chicago
Cheap Flights: Chicago to Zagreb, Croatia, Sofia, Bulgaria, or Belgrade, Serbia $645-$678 round-trip [Oct-Dec, Feb / Oct-Dec, Feb-May / Nov] (No Holidays) – LOT
LOT has round-trip flights from Chicago (ORD) to Zagreb, Croatia, Sofia, Bulgaria, or Belgrade, Serbia (ZAG, SOF, BEG) for $645-$678 with a connection. Holiday blackouts. Croatia: Flights October to D...
escape.flights
September 8, 2026 at 4:18 PM
chi.escape.flights
Nonstop Flights: Chicago to/from St. Louis, Cleveland, or Minneapolis $117 round-trip [September-March] (STL/MSP Thanksgiving availability) - Southwest

escape.flights?p=66845

#Airfare #Flights #Travel #EscapeFlights #Chicago
Nonstop Flights: Chicago to/from St. Louis, Cleveland, or Minneapolis $117 round-trip [September-March] (STL/MSP Thanksgiving availability) – Southwest
[09/07/2026 @ 07:06 PM CT] Deal time-stamp. To book: Use our updated link list. Southwest has round-trip flights from Chicago (MDW) to St. Louis, Cleveland, or Minneapolis (STL, CLE, MSP)…
escape.flights
September 8, 2026 at 12:20 AM
chi.escape.flights
Nonstop Flights: Chicago to/from Seattle $197 round-trip [Oct-Mar] (Holiday availability) - Delta

This fare has Christmas availability, which is rare at this price.

escape.flights?p=66752

#Airfare #Flights #Travel #EscapeFlights #Chicago
September 4, 2026 at 1:20 PM
chi.escape.flights
Nonstop Flights: Chicago to/from San Juan $217 round-trip [September-December] (No Holidays) - United

Not bad...

escape.flights?p=66741

#Airfare #Flights #Travel #EscapeFlights #Chicago
September 4, 2026 at 3:16 AM