Escape Flights - Chicago/MKE (2024)

28/06/2024

https://escape.flights/?p=52447

Links to these fares are available on our website, in the full blog post.

Deals usually last about 24-72 hours after posting.

Typo fixed: Removed other destinations. This fare applies to Rome only.

Icelandair has round-trip flights from Chicago (ORD) to Rome (FCO) for $398 with a connection. Flights November to March. No Major Holiday dates.

Some small OTAs on Skyscanner and Google have this for as low as $367; which is cheaper than the airline. If you plan on booking there, beware of any site that charges a fee to cancel a ticket within the 24-hour "free" period. Use unknown booking sites at your own risk.

A Carry on bag (20-lbs @ 21.6 x 15.7 x 7.8 inches) and a personal item (15.7 x 11.8 x 5.9 inches) is allowed for free on Icelandair. You can avoid seat selection fees by accepting the randomly assigned seat at the gate.

Icelandair offers free stopovers, which good if you want spend a few nights in Reykjavik. More details are on their website (link).

28/06/2024

https://escape.flights/?p=52442

Links to these fares are available on our website, in the full blog post.

Deals usually last about 24-72 hours after posting.

American, Alaska Airlines, and Southwest have round-trip flights from Milwaukee (MKE) to Kailua-Kona, Hawaii (KOA) for $360-$400 with a connection. $180-$220 each-way. Flights August to October.

You may have to book this one as two separate one-ways. The outbound flight is on American or Alaska Airlines, the return flight is on Southwest.

A Carry-on bag and also a personal item is allowed for free. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.

Want a notification sent straight to your phone when any new deals are found? Join our Telegram channel and never miss another deal.

Our website wouldn't be possible without the direct financial support from our Patreons. If you like the work that we do, then consider becoming a Patreon supporter. We send our supporters an additional daily recap of every fare below the 6-month moving average.

We don't charge a subscription fee. All our deal notifications are available for FREE via Instagram, Mastodon, Facebook, Twitter, Telegram, our Webpage, and our E-mail list. If you are paying someone a subscription fee for this content, you are being ripped off.

27/06/2024

https://escape.flights/?p=52393

Links to these fares are available on our website, in the full blog post.

Deals usually last about 24-72 hours after posting.

American Airlines has round-trip flights from Chicago (ORD) to Kahului (OGG) for $350 with a connection. Flights August to November. Departures on Monday, Tuesday, Wednesday, and Sunday. No Thanksgiving dates.

A Carry-on bag and also a personal item is allowed for free on American. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.

Want a notification sent straight to your phone when any new deals are found? Join our Telegram channel and never miss another deal.

Our website wouldn't be possible without the direct financial support from our Patreons. If you like the work that we do, then consider becoming a Patreon supporter. We send our supporters an additional daily recap of every fare below the 6-month moving average.

We don't charge a subscription fee. All our deal notifications are available for FREE via Instagram, Mastodon, Facebook, Twitter, Telegram, our Webpage, and our E-mail list. If you are paying someone a subscription fee for this content, you are being ripped off.

27/06/2024

https://escape.flights/?p=52390

Links to these fares are available on our website, in the full blog post.

Deals usually last about 24-72 hours after posting.

United has round-trip flights from Chicago or Milwaukee (ORD, MKE) to Denver (DEN) for $137-$146, NONSTOP. Flights August to December. Very few weekends available. Origin/Destination reversible. No Christmas dates available.

United's "Basic Economy" fares do not allow for a free carry-on bag. Only a personal item (like a small laptop bag) is free. Seats are randomly assigned for free prior to boarding.

The personal item size on United is smaller (9 x 10 x 17 inches) than Frontier or Spirit (8 x 13 x 18 inches).

Want a notification sent straight to your phone when any new deals are found? Join our Telegram channel and never miss another deal.

Our website wouldn't be possible without the direct financial support from our Patreons. If you like the work that we do, then consider becoming a Patreon supporter. We send our supporters an additional daily recap of every fare below the 6-month moving average.

We don't charge a subscription fee. All our deal notifications are available for FREE via Instagram, Mastodon, Facebook, Twitter, Telegram, our Webpage, and our E-mail list. If you are paying someone a subscription fee for this content, you are being ripped off.

24/06/2024

https://escape.flights/?p=52341

Links to these fares are available on our website, in the full blog post.

Deals usually last about 24-72 hours after posting.

WestJet has round-trip flights from Chicago (ORD) to Calgary, Vancouver, Regina, Kelowna, Victoria, Canada (YYC, YVR, YQR, YLW, YYJ) for $176-$279. Flights August to September. Origin/Destination reversible.

Calgary flights are Nonstop. Other destinations have a connection.

Want a notification sent straight to your phone when any new deals are found? Join our Telegram channel and never miss another deal.

Our website wouldn't be possible without the direct financial support from our Patreons. If you like the work that we do, then consider becoming a Patreon supporter. We send our supporters an additional daily recap of every fare below the 6-month moving average.

We don't charge a subscription fee. All our deal notifications are available for FREE via Instagram, Mastodon, Facebook, Twitter, Telegram, our Webpage, and our E-mail list. If you are paying someone a subscription fee for this content, you are being ripped off.

19/06/2024

https://escape.flights/?p=52292

Links to these fares are available on our website, in the full blog post.

Deals usually last about 24-72 hours after posting.

Icelandair has round-trip flights from Chicago (ORD) to Barcelona or Dublin (BCN, DUB) for $383-$439 with a connection. Flights September to March.

A Carry on bag (20-lbs @ 21.6 x 15.7 x 7.8 inches) and a personal item (15.7 x 11.8 x 5.9 inches) is allowed for free on Icelandair. You can avoid seat selection fees by accepting the randomly assigned seat at the gate.

Icelandair offers free stopovers, which good if you want spend a few nights in Reykjavik. More details are on their website (link).

Want a notification sent straight to your phone when any new deals are found? Join our Telegram channel and never miss another deal.

Our website wouldn't be possible without the direct financial support from our Patreons. If you like the work that we do, then consider becoming a Patreon supporter. We send our supporters an additional daily recap of every fare below the 6-month moving average.

We don't charge a subscription fee. All our deal notifications are available for FREE via Instagram, Mastodon, Facebook, Twitter, Telegram, our Webpage, and our E-mail list. If you are paying someone a subscription fee for this content, you are being ripped off.

19/06/2024

https://escape.flights/?p=52289

Links to these fares are available on our website, in the full blog post.

Deals usually last about 24-72 hours after posting.

Delta, JetBlue, and United have round-trip flights from New York/Newark (LGA/JFK/EWR) to Chicago (ORD) for $109-$118, NONSTOP. Flights in July. No Saturday departures. Very few weekends available. Origin/Destination reversible.

A Carry-on bag and also a personal item is allowed for free on Delta. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.

14/06/2024

https://escape.flights/?p=52262

Links to these fares are available on our website, in the full blog post.

Deals usually last about 24-72 hours after posting.

JetBlue has round-trip flights from Chicago (ORD) to London, United Kingdom (LGW) for $476-$500 with a connection. Flights in September. Departures on Tuesday, Wednesday, and Thursday. Very few extended weekends available.

JetBlue's "Basic" fares only allow a small personal item (17 x 13 x 8 inches), like a Jansport SuperBreak backpack without a fee. A regular sized carry-on bag will incur a bag fee. To avoid bag fees, consider using a credit card with the "first free checked bag" perk.

13/06/2024

https://escape.flights/?p=52233

Links to these fares are available on our website, in the full blog post.

Deals usually last about 24-72 hours after posting.

United, Delta, and American have round-trip flights from Chicago (ORD) to San Francisco, Salt Lake City, or San Diego (SFO, SLC, SAN) for $117-$144, NONSTOP. Flights August to December. Extended weekends available. Origin/Destination reversible. No Christmas dates available.

United's "Basic Economy" fares do not allow for a free carry-on bag. Only a personal item (like a small laptop bag) is free. Seats are randomly assigned for free prior to boarding.

The personal item size on United is smaller (9 x 10 x 17 inches) than Frontier or Spirit (8 x 13 x 18 inches).

13/06/2024

https://escape.flights/?p=52227

Links to these fares are available on our website, in the full blog post.

Deals usually last about 24-72 hours after posting.

American, United, and Southwest have round-trip flights from Chicago (ORD) to Austin, Tampa, Miami, San Antonio, Tampa, Nashville, or Philadelphia (AUS, TPA, MIA, SAT, TPA, ATL, BNA, PHL) for $75-$97, NONSTOP. Flights August to December. Departures on Tuesday, Wednesday, and Saturday. Extended weekends available. Origin/Destination reversible. No Christmas dates available.

A Carry-on bag and also a personal item is allowed for free on American and Southwest. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.

This is part of the Domestic Airfare sale that we mentioned a few days ago. There are more destinations on sale than this one that we are highlighting.

Want a notification sent straight to your phone when any new deals are found? Join our Telegram channel and never miss another deal.

Our website wouldn't be possible without the direct financial support from our Patreons. If you like the work that we do, then consider becoming a Patreon supporter. We send our supporters an additional daily recap of every fare below the 6-month moving average.

We don't charge a subscription fee. All our deal notifications are available for FREE via Instagram, Mastodon, Facebook, Twitter, Telegram, our Webpage, and our E-mail list. If you are paying someone a subscription fee for this content, you are being ripped off.

12/06/2024

https://escape.flights/?p=52189

Links to these fares are available on our website, in the full blog post.

Deals usually last about 24-72 hours after posting.

Icelandair has round-trip flights from Chicago (ORD) to Amsterdam, Berlin, Manchester, or London (AMS, BER, MAN, LHR) for $462-$517 with a connection. Flights September to April. Extended weekends available.

Some small OTAs on Skyscanner and Google have this for about 5% to 8% cheaper than the airline. If you plan on booking there, beware of any site that charges a fee to cancel a ticket within the 24-hour "free" period. Use unknown booking sites at your own risk.

A Carry on bag (20-lbs @ 21.6 x 15.7 x 7.8 inches) and a personal item (15.7 x 11.8 x 5.9 inches) is allowed for free on Icelandair. You can avoid seat selection fees by accepting the randomly assigned seat at the gate.

Icelandair offers free stopovers, which good if you want spend a few nights in Reykjavik. More details are on their website (link).

Want a notification sent straight to your phone when any new deals are found? Join our Telegram channel and never miss another deal.

Our website wouldn't be possible without the direct financial support from our Patreons. If you like the work that we do, then consider becoming a Patreon supporter. We send our supporters an additional daily recap of every fare below the 6-month moving average.

We don't charge a subscription fee. All our deal notifications are available for FREE via Instagram, Mastodon, Facebook, Twitter, Telegram, our Webpage, and our E-mail list. If you are paying someone a subscription fee for this content, you are being ripped off.

12/06/2024

https://escape.flights/?p=52176

Links to these fares are available on our website, in the full blog post.

Deals usually last about 24-72 hours after posting.

Frontier has round-trip flights from Chicago (MDW) to San Francisco or Las Vegas (SFO, LAS) for $38-$45, NONSTOP. Flights August to October. Origin/Destination reversible.

Frontier fares do not include a free carry-on bag. Only a small personal item, like a Jansport SuperBreak backpack is free. You can avoid paying for seat selection if you accept the randomly assigned seat prior to boarding.

Frontier seats only have 28-inches of pitch; 2-to-3 inches less space than most other airlines.

Want a notification sent straight to your phone when any new deals are found? Join our Telegram channel and never miss another deal.

Our website wouldn't be possible without the direct financial support from our Patreons. If you like the work that we do, then consider becoming a Patreon supporter. We send our supporters an additional daily recap of every fare below the 6-month moving average.

We don't charge a subscription fee. All our deal notifications are available for FREE via Instagram, Mastodon, Facebook, Twitter, Telegram, our Webpage, and our E-mail list. If you are paying someone a subscription fee for this content, you are being ripped off.

12/06/2024

https://escape.flights/?p=52165

Links to these fares are available on our website, in the full blog post.

Deals usually last about 24-72 hours after posting.

United has round-trip flights from Chicago (ORD) to Cancun, Tulum, or San Jose del Cabo (CUN, TQO, SJD) for $223-$314, NONSTOP. Flights September to December. Origin/Destination reversible. No Christmas dates available.

Cabo is the most expensive fare in this group. Expect to pay around $295.

United's "Basic Economy" fares do not allow for a free carry-on bag. Only a personal item (like a small laptop bag) is free. Seats are randomly assigned for free prior to boarding.

The personal item size on United is smaller (9 x 10 x 17 inches) than Frontier or Spirit (8 x 13 x 18 inches).

Want a notification sent straight to your phone when any new deals are found? Join our Telegram channel and never miss another deal.

Our website wouldn't be possible without the direct financial support from our Patreons. If you like the work that we do, then consider becoming a Patreon supporter. We send our supporters an additional daily recap of every fare below the 6-month moving average.

We don't charge a subscription fee. All our deal notifications are available for FREE via Instagram, Mastodon, Facebook, Twitter, Telegram, our Webpage, and our E-mail list. If you are paying someone a subscription fee for this content, you are being ripped off.

12/06/2024

https://escape.flights/?p=52125

Links to these fares are available on our website, in the full blog post.

Deals usually last about 24-72 hours after posting.

American Airlines has round-trip flights from Chicago (ORD) to Nassau, Bahamas or Providenciales, Turks & Caicos Islands (NAS, PLS) for $288-$322, NONSTOP. Flights August to December. Weekends available. Origin/Destination reversible. No Christmas dates available.

A Carry-on bag and also a personal item is allowed for free on American. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.

Want a notification sent straight to your phone when any new deals are found? Join our Telegram channel and never miss another deal.

Our website wouldn't be possible without the direct financial support from our Patreons. If you like the work that we do, then consider becoming a Patreon supporter. We send our supporters an additional daily recap of every fare below the 6-month moving average.

We don't charge a subscription fee. All our deal notifications are available for FREE via Instagram, Mastodon, Facebook, Twitter, Telegram, our Webpage, and our E-mail list. If you are paying someone a subscription fee for this content, you are being ripped off.

11/06/2024

https://escape.flights/?p=52114

Links to these fares are available on our website, in the full blog post.

Deals usually last about 24-72 hours after posting.

American Airlines has round-trip flights from Chicago (ORD) to Puerto Vallarta or Montego Bay, Jamaica (PVR, MBJ) for $293-$330, NONSTOP. Puerto Vallarta flights November to December. Montego Bay flights in August, November, and December. Origin/Destination reversible. Holiday blackouts.

A Carry-on bag and also a personal item is allowed for free on American. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.

Want a notification sent straight to your phone when any new deals are found? Join our Telegram channel and never miss another deal.

Our website wouldn't be possible without the direct financial support from our Patreons. If you like the work that we do, then consider becoming a Patreon supporter. We send our supporters an additional daily recap of every fare below the 6-month moving average.

We don't charge a subscription fee. All our deal notifications are available for FREE via Instagram, Mastodon, Facebook, Twitter, Telegram, our Webpage, and our E-mail list. If you are paying someone a subscription fee for this content, you are being ripped off.

11/06/2024

https://escape.flights/?p=50065

This list intentionally excludes fares on LCC Breeze/Allegiant/Frontier/Spirit.

Links to these fares are available on our website, in the full blog post.

Deals usually last about 24-72 hours after posting.

Most domestic carriers have round-trip flights to/from various destinations in the USA at a discount today for $74-$185, NONSTOP or with a connection. Dates vary, use the linked calendar. American and Southwest are mostly on Tuesdays, Wednesdays, and Saturdays. United has better weekend availability. Origin/Destination reversible.

For Southwest fares, you may need to plug-in the coupon-code “BDAY”. You should be able to see the fares on the calendar, linked, without using the code.

There are other destinations available that are priced higher than this range and those may be worthwhile for some of the small remote airports that have stops and don't usually go on sale. They aren't part of this list since we're focusing on the cheapest routes.

When these type of “wide” sales happen, they are often matched by other airlines eventually.

Want a notification sent straight to your phone when any new deals are found? Join our Telegram channel and never miss another deal.

Our website wouldn't be possible without the direct financial support from our Patreons. If you like the work that we do, then consider becoming a Patreon supporter. We send our supporters an additional daily recap of every fare below the 6-month moving average.

We don't charge a subscription fee. All our deal notifications are available for FREE via Instagram, Mastodon, Facebook, Twitter, Telegram, our Webpage, and our E-mail list. If you are paying someone a subscription fee for this content, you are being ripped off.

11/06/2024

https://escape.flights/?p=52085

Links to these fares are available on our website, in the full blog post.

Deals usually last about 24-72 hours after posting.

Southwest and United have round-trip flights from Chicago (ORD, MDW) to St. Louis, Salt Lake City, Sacramento, San Antonio, San Jose, CA, or Rochester, NY (STL, SLC, SMF, SAT, SJC, ROC) for $105-$114, NONSTOP. Flights August to December. Weekends available. Origin/Destination reversible. No Christmas dates available.

Note: Southwest is matching on some of these routes but to get the discount requires jumping through a few annoying hoops. First, you can only see the fare in their slow and buggy Southwest (mobile phone) App. Second, you have to use code “BDAY”.

United's "Basic Economy" fares do not allow for a free carry-on bag. Only a personal item (like a small laptop bag) is free. Seats are randomly assigned for free prior to boarding.

The personal item size on United is smaller (9 x 10 x 17 inches) than Frontier or Spirit (8 x 13 x 18 inches).

Want a notification sent straight to your phone when any new deals are found? Join our Telegram channel and never miss another deal.

Our website wouldn't be possible without the direct financial support from our Patreons. If you like the work that we do, then consider becoming a Patreon supporter. We send our supporters an additional daily recap of every fare below the 6-month moving average.

We don't charge a subscription fee. All our deal notifications are available for FREE via Instagram, Mastodon, Facebook, Twitter, Telegram, our Webpage, and our E-mail list. If you are paying someone a subscription fee for this content, you are being ripped off.

10/06/2024

https://escape.flights/?p=52056

Links to these fares are available on our website, in the full blog post.

Deals usually last about 24-72 hours after posting.

Delta has round-trip flights from Milwaukee (MKE) to San Jose, Costa Rica (SJO) for $316-$331 with a connection. Flights October, November, January, and February. Departures on Monday, Tuesday, and Sunday. Origin/Destination reversible. No Thanksgiving dates.

A Carry-on bag and also a personal item is allowed for free on Delta. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.

Want a notification sent straight to your phone when any new deals are found? Join our Telegram channel and never miss another deal.

Our website wouldn't be possible without the direct financial support from our Patreons. If you like the work that we do, then consider becoming a Patreon supporter. We send our supporters an additional daily recap of every fare below the 6-month moving average.

We don't charge a subscription fee. All our deal notifications are available for FREE via Instagram, Mastodon, Facebook, Twitter, Telegram, our Webpage, and our E-mail list. If you are paying someone a subscription fee for this content, you are being ripped off.

08/06/2024

https://escape.flights/?p=51133

We update our list of the best limited time offers every week, but we only send out this recap when there have been significant additions to the list. In this post we list coupon codes, discount codes, gift card discounts, and we watch for increases in credit card offers.

Links and up-to-date details for these offers are on our website.

08/06/2024

https://escape.flights/?p=52033

Links to these fares are available on our website, in the full blog post.

Deals usually last about 24-72 hours after posting.

American Airlines and Southwest have round-trip flights from Chicago (ORD/MDW) to Miami (MIA) for $137, NONSTOP. Flights August to November. No Monday departures. Extended weekends available. Origin/Destination reversible. No Thanksgiving dates.

A Carry-on bag and also a personal item is allowed for free on American. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.

Want a notification sent straight to your phone when any new deals are found? Join our Telegram channel and never miss another deal.

Our website wouldn't be possible without the direct financial support from our Patreons. If you like the work that we do, then consider becoming a Patreon supporter. We send our supporters an additional daily recap of every fare below the 6-month moving average.

We don't charge a subscription fee. All our deal notifications are available for FREE via Instagram, Mastodon, Facebook, Twitter, Telegram, our Webpage, and our E-mail list. If you are paying someone a subscription fee for this content, you are being ripped off.

05/06/2024

https://escape.flights/?p=52007

Links to these fares are available on our website, in the full blog post.

Deals usually last about 24-72 hours after posting.

United and American have round-trip flights from Chicago (ORD) to Seattle or Portland (SEA, PDX) for $149-$190, NONSTOP. Seattle Flights August to April. Portland flights August to November. Extended weekends available. Origin/Destination reversible.

United's "Basic Economy" fares do not allow for a free carry-on bag. Only a personal item (like a small laptop bag) is free. Seats are randomly assigned for free prior to boarding.

The personal item size on United is smaller (9 x 10 x 17 inches) than Frontier or Spirit (8 x 13 x 18 inches).

04/06/2024

https://escape.flights/?p=51963

Links to these fares are available on our website, in the full blog post.

Deals usually last about 24-72 hours after posting.

Frontier has round-trip flights from Chicago (MDW/ORD) to Atlanta (ATL) for $38-$48, NONSTOP. $19-$24 each-way. Flights July to November. No Sunday departures. Very few weekends available. Origin/Destination reversible. No Thanksgiving dates.

Frontier fares do not include a free carry-on bag. Only a small personal item, like a Jansport SuperBreak backpack is free. You can avoid paying for seat selection if you accept the randomly assigned seat prior to boarding.

Frontier seats only have 28-inches of pitch; 2-to-3 inches less space than most other airlines.

Escape Flights - Chicago/MKE

28/06/2024

28/06/2024

27/06/2024

27/06/2024

24/06/2024

19/06/2024

19/06/2024

14/06/2024

13/06/2024

13/06/2024

12/06/2024

12/06/2024

12/06/2024

12/06/2024

11/06/2024

11/06/2024

11/06/2024

10/06/2024

08/06/2024

08/06/2024

05/06/2024

04/06/2024

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