Category: <span>Flights from Chicago / Milwaukee</span>

Aer Lingus Airfare Deals Flights from Chicago / Milwaukee Milan

Tap Air Portugal and Aer Lingus have round-trip flights from Chicago (ORD) to Porto or Lisbon (OPO, LIS) for $449-$469 with a connection. Porto flights November to March. Lisbon flights October to December. No Thanksgiving dates.

Some small OTAs on Skyscanner and Google have this for 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.

Carry on bag with a maximum weight of 17.6 lbs is allowed for free on TAP. You can avoid seat selection fees by accepting the randomly assigned seat at the gate. Upgrading to a higher fare class that includes a carry-on bag for $65 may be cheaper than booking the “Discount” fare with the added $95 carry-on bag fee.

Flights on TAP allow for a free stopover (up to 5-days) in their hub city. This will be useful if you want to spend time exploring Porto or Lisbon before heading to your final destination. Link: More details on the TAP stopover program.

Click for more details and booking links Cheap Flights: Chicago to Porto or Lisbon $449-$469 r/t [Nov-Mar / Oct-Dec] (No Thanksgiving) – Tap Air Portugal / Aer Lingus

Airfare Deals Flights from Chicago / Milwaukee Porto TAP Air Portugal

Icelandair has round-trip flights from Chicago (ORD) to Zurich (ZRH) for $406 or Frankfurt (FRA) for $490 with a connection. Flights November to March. No Thanksgiving dates.

Some small OTAs on Skyscanner and Google have this for about -$50 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).

Click for more details and booking links Cheap Flights: Chicago to Zurich $359-$406 or Frankfurt $441-$490 r/t [November-March] (No Thanksgiving) – Icelandair

Airfare Deals Flights from Chicago / Milwaukee IcelandAir Zurich

Turkish Airlines has round-trip flights from Chicago (ORD) to Venice (VCE) for $548 with a connection. Flights October to March. Departures on Monday, Tuesday, Wednesday, and Sunday.

Some small OTAs on Skyscanner and Google have this for as low as $496; 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.

Click for more details and booking links Cheap Flights: Chicago to Venice $496-$548 r/t [October-March] – Turkish Airlines

Airfare Deals Flights from Chicago / Milwaukee Turkish Airlines Venice

Delta and United has round-trip flights from Chicago (ORD) to Paris or Rome (CDG, FCO) for $462-$472, NONSTOP. Paris flights October to March. Rome flights October to November. 7-day minimum stay required.

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.

Click for more details and booking links Nonstop Flights: Chicago to Paris or Rome $462-$472 r/t [Oct-Mar / Oct-Nov] – Delta / United

Airfare Deals Delta Flights from Chicago / Milwaukee Paris SkyTeam

LOT has round-trip flights from Chicago (ORD) to Zagreb (ZAG) for $509 with a connection. Flights January to March. Extended weekends available.

Some small OTAs on Skyscanner and Google have this for as low as $492; 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.

This is part of the European Airfare sale that we previously mentioned.

Carry on bag with a maximum weight of 17.6 lbs is allowed for free on LOT. You can avoid seat selection fees by accepting the randomly assigned seat at the gate. Be advised that LOT charges about $74 each-way for a regular sized checked bag for their “Saver” fare class on their International flights to/from the USA. Upgrading to a higher fare class that includes a carry-on bag may be cheaper than booking the discount fare with the added carry-on bag fee.

Click for more details and booking links Cheap Flights: Chicago to Zagreb, Croatia $492-$509 r/t [January-March] – LOT

Airfare Deals Flights from Chicago / Milwaukee LOT Zagreb

Various carriers has round-trip flights to/from Europe at a discount today for $329-$630, NONSTOP or with a connection (see list on our website). Dates vary, use the calendar link in the post.

This list includes several discount LCC carriers. Those carriers may have additional fees for bags, seat, and meals.

Flights to/from smaller airports may require a long connection or two stops. When you begin your search, modify your filter to remove fares that have more than one connection, some of those smaller airports ONLY have flights with bad routing.

Some small OTAs on Skyscanner and Google have this for 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.

Click for more details and booking links European Airfare Sale: to/from various European destinations $329-$630 r/t [dates vary, mostly between October and March] – Various Airlines including LCCs

Aer Lingus Airfare Deals Alaska Airlines Delta Flights from Atlanta Flights from Chicago / Milwaukee Flights from Denver Flights from Los Angeles Flights from Milwaukee Flights from New York Flights from Phoenix Flights from Portland Flights from Seattle San Francisco SkyTeam Star Alliance United

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 in this post.

(Ends 09-05-2024) Southwest 2-month Companion Pass. Register, then purchase one round trip or two one-way flights by 09/05/24. Travel by 11/20/24. Companion flies free with you 01/06/25 – 03/06/25.

(Ends 09-05-2024 @ 11:59 PM PT) 50% off base fares on Breeze. Use code “BIGDEAL”. Holiday blackouts apply.

(Ending 09-05-2024 @ 7am EST!) 120,000 points after spending $8,000 in the first 3-months of being approved for one of the best business card deals we’ve seen.

The coupon-code page on our website is updated often, consider bookmaking it for easy access.

Click for more details and booking links Our updated list of coupon codes, discount codes, gift card discounts, and credit card bonuses as of 09/03/2024

Administrative Airfare Deals Flights from Atlanta Flights from Chicago / Milwaukee Flights from Denver Flights from Los Angeles Flights from Milwaukee Flights from New York Flights from Phoenix Flights from Portland Flights from Seattle Miles and Points

Cathay Pacific has round-trip flights from Chicago (ORD) to Manila (MNL) for $811 with a connection. Flights September, October, February, and March. No Weekends. Departures on Monday, Tuesday, Wednesday, and Thursday.

Some small OTAs on Skyscanner and Google have this as low as $770; which is for 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.

Click for more details and booking links Cheap Flights: Chicago to Manila $770-$811 r/t [Sep-Oct, Feb-Mar] – Cathay Pacific

Airfare Deals Cathay Pacific Flights from Chicago / Milwaukee Manila Oneworld

Icelandair has round-trip flights from Chicago (ORD) to London, United Kingdom (LGW/LHR) for $507-$516 with a connection. Flights November, December, January, February, and April. Extended weekends available. Origin/Destination reversible. Holiday blackouts.

Some small OTAs on Skyscanner and Google have this for as low as $461; 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).

Click for more details and booking links Cheap Flights: Chicago to/from London, United Kingdom $461-$516 r/t (No Christmas / Thanksgiving) – Icelandair

Airfare Deals Flights from Chicago / Milwaukee IcelandAir London United Kingdom

Icelandair has round-trip flights from Chicago (ORD) to Barcelona, Copenhagen, Oslo, Rome, Berlin, Dublin, Paris, or Stockholm (BCN, CPH, OSL, FCO, BER, DUB, CDG, ARN) for $339-$464 with a connection. Flights October to February. 

Some small OTAs on Skyscanner and Google have this for 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).

Click for more details and booking links Cheap Flights: Chicago to Barcelona, Copenhagen, Oslo, Rome, Berlin, Dublin, Paris, or Stockholm $339-$464 r/t [October-February] – Icelandair

Airfare Deals Barcelona Flights from Chicago / Milwaukee IcelandAir

Delta and LATAM have round-trip flights from Milwaukee (MKE) to Sao Paulo, Santiago, or Rio de Janeiro (GRU, SCL, GIG) for $656-$691 with a connection. Flights October to December. Extended weekends available. Origin/Destination reversible. No Christmas dates available.

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.

Click for more details and booking links Cheap Flights: Milwaukee to/from Sao Paulo, Santiago, or Rio de Janeiro $656-$691 r/t [October-December] (No Christmas) – Delta / LATAM

Airfare Deals Delta Flights from Chicago / Milwaukee Flights from Milwaukee LATAM Oneworld Sao Paulo SkyTeam

American Airlines and Qantas have round-trip flights from Chicago (ORD) to Sydney, Australia (SYD) for $858 with a connection. Flights October, November, February, and March. Extended weekends available. No Thanksgiving dates.

Some small OTAs on Skyscanner and Google have this for as low as $787; 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 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.

Click for more details and booking links Cheap Flights: Chicago to Sydney, Australia $787-$858 r/t [Oct-Nov, Feb-Mar] (No Thanksgiving) – American Airlines / Qantas

Airfare Deals American Airlines Australia Flights from Chicago / Milwaukee Oneworld Sydney

Image Credits: Public Domain

United has round-trip flights from Chicago (ORD) to Montego Bay (MBJ) for $317, NONSTOP. Flights October to February. Departures on Monday, Tuesday, and Sunday. 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).

Click for more details and booking links Nonstop Flights: Chicago to/from Montego Bay $317 r/t [October-February] – United

Airfare Deals Flights from Chicago / Milwaukee Montego Bay Star Alliance United

Per Reddit: Skymiles sale to Tokyo (link).

Delta has round-trip flights from to Tokyo (HND) for 20,000 to 40,000 SkyMiles and $6 to $51 in fees each-way. Flights were seen between September and December, but there may be additional or less availability depending on your origin airport.

A Carry-on bag and also a personal item is allowed for free on Delta.

With most Delta co-branded cards you can get an additional 15% discount on the amount of SkyMiles you spend when you redeem them. Visit the CardRatings.com website for a list of the best travel rewards credit card offers (link).

Click for more details and booking links Delta SkyMiles: to/from Tokyo, Haneda 20,000-40,000 Delta SkyMiles each-way, $6 to $51 in fees [September-December]

Airfare Deals Delta Flights from Atlanta Flights from Chicago / Milwaukee Flights from Denver Flights from Los Angeles Flights from Milwaukee Flights from New York Flights from Phoenix Flights from Portland Flights from Seattle Helsinki SkyTeam

Tap Air Portugal has round-trip flights from Chicago (ORD) to Barcelona (BCN) for $366 with a connection. Flights October to March. Departures on Wednesday. 7-day minimum stay required.

Some small OTAs on Skyscanner and Google have this for as low as $327; 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.

Carry on bag with a maximum weight of 17.6 lbs is allowed for free on TAP. You can avoid seat selection fees by accepting the randomly assigned seat at the gate. Upgrading to a higher fare class that includes a carry-on bag for $65 may be cheaper than booking the “Discount” fare with the added $95 carry-on bag fee.

Flights on TAP allow for a free stopover (up to 5-days) in their hub city. This will be useful if you want to spend time exploring Porto or Lisbon before heading to your final destination. Link: More details on the TAP stopover program.

Click for more details and booking links Cheap Flights: Chicago to Barcelona $327-$366 r/t [October-March] – Tap Air Portugal

Airfare Deals Barcelona Flights from Chicago / Milwaukee TAP Air Portugal

United has round-trip flights from Portland (PDX) to Chicago (ORD) for $137-$166, NONSTOP. Flights September 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).

Click for more details and booking links Nonstop Flights: Portland to/from Chicago $137-$166 r/t [September-December] (No Christmas) – United

Airfare Deals Chicago Flights from Chicago / Milwaukee Flights from Portland Star Alliance United

Airfare Deals Flights from Chicago / Milwaukee Grand Rapids Star Alliance United

Alaska Airlines has round-trip flights from Seattle (SEA) to Chicago (ORD) for $137, NONSTOP. Flights September to December. Departures on Monday, Tuesday, Wednesday, Thursday, and Saturday. Extended weekends available. Origin/Destination reversible. No Christmas dates available.

Some small OTAs on Skyscanner and Google have this for as low as $124; 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 and also a personal item is allowed for free on Alaska Airlines. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.

Click for more details and booking links Nonstop Flights: Seattle to/from Chicago $124-$137 r/t [September-December] (No Christmas) – Alaska Airlines

Airfare Deals Alaska Airlines Chicago Flights from Chicago / Milwaukee Flights from Seattle

Airfare Deals Cleveland Flights from Chicago / Milwaukee Southwest