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

Cheap Flights: Chicago to Glasgow $495-$543 r/t [January-May] – Icelandair
Image Credits: cattan2011, Creative Commons 2.0 (flickr)
Published December 3, 2024 by

Cheap Flights: Chicago to Glasgow $495-$543 r/t [January-May] – Icelandair

Icelandair has round-trip flights from Chicago (ORD) to Glasgow (GLA) for $529-$543 with a connection. Flights January to May. No Wednesday departures. Extended weekends available.

Some small OTAs on Skyscanner and Google have this for as low as $495; 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.

Click for more details and booking links Cheap Flights: Chicago to Glasgow $495-$543 r/t [January-May] – Icelandair

Airfare Deals Flights from Chicago / Milwaukee Glasgow IcelandAir

Cheap Flights: Chicago to Rio de Janeiro $537 r/t [January] – American Airlines
Image Credits: selbst fotografiert von, creative commons 3.0
Published December 3, 2024 by

Cheap Flights: Chicago to Rio de Janeiro $537 r/t [January] – American Airlines

Airfare Deals American Airlines Flights from Chicago / Milwaukee Oneworld Rio de Janeiro

Nonstop Flights: Chicago to Denver $38-$55 r/t [December-March] (No Christmas) (budget carrier) – Frontier
Image Credits: Larry Johnson, Creative Commons 2.0
Published December 2, 2024 by

Nonstop Flights: Chicago to Denver $38-$55 r/t [December-March] (No Christmas) (budget carrier) – Frontier

Frontier has round-trip flights from Chicago (MDW) to Denver (DEN) for $38-$55, NONSTOP. Flights December to March. Departures on Monday, Tuesday, Wednesday, Thursday, and Saturday. Extended weekends available. No Christmas dates available.

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.

Click for more details and booking links Nonstop Flights: Chicago to Denver $38-$55 r/t [December-March] (No Christmas) (budget carrier) – Frontier

Airfare Deals Denver Flights from Chicago / Milwaukee Frontier

Nonstop Flights: Chicago to New York $117 r/t [December-April] (No Christmas) – JetBlue / American
Image Credits: Thomas Hawk, Creative Commons 2.0 (flickr)
Published December 2, 2024 by

Nonstop Flights: Chicago to New York $117 r/t [December-April] (No Christmas) – JetBlue / American

JetBlue and American have round-trip flights from Chicago (ORD) to New York (JFK) for $117, NONSTOP. Flights December to April. Departures on Monday, Tuesday, Wednesday, Thursday, and Saturday. Extended weekends available. No Christmas dates available.

JetBlue’s “Basic” fares allow for a carry-on bag and a small personal item (17 x 13 x 8 inches), like a Jansport SuperBreak backpack without a fee. You can avoid seat selection fees by accepting the randomly assigned seat at the gate.

Click for more details and booking links Nonstop Flights: Chicago to New York $117 r/t [December-April] (No Christmas) – JetBlue / American

Airfare Deals Flights from Chicago / Milwaukee JetBlue New York

Nonstop Flights: Chicago to Seattle $128 or Portland Oregon $168 r/t [January-March] – Southwest / Delta / Alaska Airlines
Image Credits: Howard Ignatius, Creative Commons 2.0 (flickr)
Published November 29, 2024 by

Nonstop Flights: Chicago to Seattle $128 or Portland Oregon $168 r/t [January-March] – Southwest / Delta / Alaska Airlines

Airfare Deals Flights from Chicago / Milwaukee Seattle Southwest

Cheap Flights: Chicago to Brisbane, Australia $680 r/t [January-March] – American Airlines / Qantas
Image Credits: Andrew Sutherland, Creative Commons 2.0 (flickr)
Published November 27, 2024 by

Cheap Flights: Chicago to Brisbane, Australia $680 r/t [January-March] – American Airlines / Qantas

Airfare Deals American Airlines Brisbane Flights from Chicago / Milwaukee Oneworld

Cheap Flights: Chicago to Rome or Berlin $422-$452 r/t [January-February] – Icelandair
Image Credits: David Evers, Creative Commons 2.0
Published November 27, 2024 by

Cheap Flights: Chicago to Rome or Berlin $422-$452 r/t [January-February] – Icelandair

Icelandair has round-trip flights from Chicago (ORD) to Rome or Berlin (FCO, BER) for $422-$511 with a connection. Flights January to February.

Some small OTAs on Skyscanner and Kayak 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.

Click for more details and booking links Cheap Flights: Chicago to Rome or Berlin $422-$452 r/t [January-February] – Icelandair

Airfare Deals Flights from Chicago / Milwaukee IcelandAir Rome

Nonstop Flights: Chicago to Calgary $124-$157 r/t [February-April] – WestJet / Skyscanner
Image Credits: Mpr001, Creative Commons 3.0 (wikipedia)
Published November 25, 2024 by

Nonstop Flights: Chicago to Calgary $124-$157 r/t [February-April] – WestJet / Skyscanner

WestJet has round-trip flights from Chicago (ORD) to Calgary (YYC) for $157, NONSTOP. Flights February to April. Departures on Monday, Thursday, and Sunday. 7-day minimum stay required.

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.

Click for more details and booking links Nonstop Flights: Chicago to Calgary $124-$157 r/t [February-April] – WestJet / Skyscanner

Airfare Deals Calgary Flights from Chicago / Milwaukee WestJet

Cheap Flights: Chicago to Amsterdam $387-$408 r/t [January-April] – Scandinavian Airlines / Skyscanner
Published November 25, 2024 by

Cheap Flights: Chicago to Amsterdam $387-$408 r/t [January-April] – Scandinavian Airlines / Skyscanner

Scandinavian Airlines has round-trip flights from Chicago (ORD) to Amsterdam (AMS) for $395-$408 with a connection. Flights January to April. Departures on Monday and Sunday. 7-day minimum stay required.

Some small OTAs on Skyscanner and Google have this for as low as $387; 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 18 lbs is allowed for free on SAS. You can avoid seat selection fees by accepting the randomly assigned seat at the gate. Upgrading to a higher fare class that includes a full-size carry-on bag for about $35 may be cheaper than booking the discount fare with the added carry-on bag fee (for about $70).

Click for more details and booking links Cheap Flights: Chicago to Amsterdam $387-$408 r/t [January-April] – Scandinavian Airlines / Skyscanner

Airfare Deals Amsterdam Flights from Chicago / Milwaukee Scandinavian Airlines

Cheap Flights: Chicago to London, United Kingdom $429-$446 r/t [January-April] – Scandinavian Airlines / Skyscanner
Image Credits: E01, Creative Commons 2.0 (flickr)
Published November 25, 2024 by

Cheap Flights: Chicago to London, United Kingdom $429-$446 r/t [January-April] – Scandinavian Airlines / Skyscanner

Scandinavian Airlines has round-trip flights from Chicago (ORD) to London, United Kingdom (LHR) for $446 with a connection. Flights January to April. Departures on Monday, Tuesday, and Sunday. 7-day minimum stay required.

Some small OTAs on Skyscanner and Google have this for as low as $429; 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 London, United Kingdom $429-$446 r/t [January-April] – Scandinavian Airlines / Skyscanner

Airfare Deals Flights from Chicago / Milwaukee London Scandinavian Airlines United Kingdom

Cheap Flights: Chicago to Fresno, Pensacola, Panama City Florida, Portland Maine, or Reno $158-$177 r/t [January-March] – American Airlines
Image Credits: Captured Visuals, Creative Commons 2.0 (flickr)
Published November 23, 2024 by

Cheap Flights: Chicago to Fresno, Pensacola, Panama City Florida, Portland Maine, or Reno $158-$177 r/t [January-March] – American Airlines

American Airlines has round-trip flights from Chicago (ORD) to Fresno, Pensacola, Panama City Florida, Portland Maine, or Reno (FAT, PNS, ECP, PWM, RNO) for $158-$177 with a connection. Flights January to March. Extended weekends 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.

Click for more details and booking links Cheap Flights: Chicago to Fresno, Pensacola, Panama City Florida, Portland Maine, or Reno $158-$177 r/t [January-March] – American Airlines

Airfare Deals American Airlines Flights from Chicago / Milwaukee Fresno Oneworld

Nonstop Flights: Chicago to Dallas $139-$169 r/t [December-March] (No Christmas) – United / Southwest
Image Credits: Raging Wire, Creative Commons 2.0 (flickr)
Published November 21, 2024 by

Nonstop Flights: Chicago to Dallas $139-$169 r/t [December-March] (No Christmas) – United / Southwest

United and Southwest have round-trip flights from Chicago (ORD, MDW) to Dallas (DFW, DAL) for $139-$169, NONSTOP. Flights December to March. Extended weekends available. 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: Chicago to Dallas $139-$169 r/t [December-March] (No Christmas) – United / Southwest

Airfare Deals Dallas Flights from Chicago / Milwaukee Star Alliance United

Cheap Flights: Chicago to Sao Paulo $507 r/t [January-September] – Delta
Published November 21, 2024 by

Cheap Flights: Chicago to Sao Paulo $507 r/t [January-September] – Delta

Delta has round-trip flights from Chicago (MDW/ORD) to Sao Paulo (GRU) for $507 with a connection. Flights January to September. No Weekends. Departures on Monday, Tuesday, Wednesday, and Thursday. 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 Cheap Flights: Chicago to Sao Paulo $507 r/t [January-September] – Delta

Airfare Deals Delta Flights from Chicago / Milwaukee Sao Paulo SkyTeam

Cheap Flights: Chicago to Brisbane $814 r/t [December-March] (Christmas dates) – American Airlines
Image Credits: Andrew Sutherland, Creative Commons 2.0 (flickr)
Published November 21, 2024 by

Cheap Flights: Chicago to Brisbane $814 r/t [December-March] (Christmas dates) – American Airlines

American Airlines has round-trip flights from Chicago (ORD) to Brisbane (BNE) for $814 with a connection. Flights December to March. Extended weekends available. Dates over Christmas are 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.

Click for more details and booking links Cheap Flights: Chicago to Brisbane $814 r/t [December-March] (Christmas dates) – American Airlines

Airfare Deals American Airlines Brisbane Flights from Chicago / Milwaukee Oneworld

Nonstop Flights: Chicago to Las Vegas $139 r/t [January-March] – American Airlines
Published November 21, 2024 by

Nonstop Flights: Chicago to Las Vegas $139 r/t [January-March] – American Airlines

Airfare Deals American Airlines Flights from Chicago / Milwaukee Las Vegas Oneworld

Nonstop Flights: Chicago to Lisbon $445-$469 r/t [January-April] – Tap Air Portugal / Skyscanner
Image Credits: mgkm photography, creative commons 2.0 (flickr)
Published November 19, 2024 by

Nonstop Flights: Chicago to Lisbon $445-$469 r/t [January-April] – Tap Air Portugal / Skyscanner

Tap Air Portugal has round-trip flights from Chicago (ORD) to Lisbon (LIS) for $469, NONSTOP. Flights January to April. 7-day minimum stay required.

Some small OTAs on Skyscanner and Kayak have this for as low as $445; 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 Nonstop Flights: Chicago to Lisbon $445-$469 r/t [January-April] – Tap Air Portugal / Skyscanner

Airfare Deals Flights from Chicago / Milwaukee Lisbon TAP Air Portugal

Cheap Flights: Chicago to Reno, Portland Maine, Pensacola, Panama City Florida, Ontario California, Charlottesville, or Fresno $178 r/t [December-February] (No Christmas) – American Airlines
Image Credits: Thomas Hawk, Creative Commons 2.0 (flickr)
Published November 13, 2024 by

Cheap Flights: Chicago to Reno, Portland Maine, Pensacola, Panama City Florida, Ontario California, Charlottesville, or Fresno $178 r/t [December-February] (No Christmas) – American Airlines

American Airlines has round-trip flights from Chicago (ORD) to Reno, Portland Maine, Pensacola, Panama City Florida, Ontario California, Charlottesville, or Fresno (RNO, PWM, PNS, ECP, ONT, CHO, FAT) for $178 with a connection. Flights December to February. Departures on Tuesday, Wednesday, and Saturday. Extended weekends available. 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.

Click for more details and booking links Cheap Flights: Chicago to Reno, Portland Maine, Pensacola, Panama City Florida, Ontario California, Charlottesville, or Fresno $178 r/t [December-February] (No Christmas) – American Airlines

Airfare Deals American Airlines Flights from Chicago / Milwaukee Oneworld Reno

Cheap Flights: Chicago to Brisbane, Australia $681 r/t [December-March] (Christmas dates) – American Airlines
Image Credits: Andrew Sutherland, Creative Commons 2.0 (flickr)
Published November 13, 2024 by

Cheap Flights: Chicago to Brisbane, Australia $681 r/t [December-March] (Christmas dates) – American Airlines

American Airlines has round-trip flights from Chicago (ORD) to Brisbane (BNE) for $681 with a connection. Flights December to March. 7-day minimum stay required. Dates over Christmas are 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.

Click for more details and booking links Cheap Flights: Chicago to Brisbane, Australia $681 r/t [December-March] (Christmas dates) – American Airlines

Airfare Deals American Airlines Brisbane Flights from Chicago / Milwaukee Oneworld

Cheap Flights: Chicago to Sydney, Australia $823-$832 r/t [January-September] – American Airlines
Image Credits: paul bica, Creative Commons 2.0 (Flickr)
Published November 13, 2024 by

Cheap Flights: Chicago to Sydney, Australia $823-$832 r/t [January-September] – American Airlines

American Airlines has round-trip flights from Chicago (ORD) to Sydney, Australia (SYD) for $823-$832 with a connection. Flights January to September. Departures on Thursday, Friday, and Saturday. 7-day minimum stay required.

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 $823-$832 r/t [January-September] – American Airlines

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

Southwest Rapid Rewards® Credit Cards: $400 statement credit and 40,000 Southwest Rapid Rewards after you spend $3,000 on purchases in the first 4 months from account opening.
Published November 12, 2024 by

Southwest Rapid Rewards® Credit Cards: $400 statement credit and 40,000 Southwest Rapid Rewards after you spend $3,000 on purchases in the first 4 months from account opening.

Chase has increased the sign-up bonus for the Southwest Rapid Rewards® Plus Credit Card and the Southwest Rapid Rewards® Priority Credit Card to 85,000 points. Bonus will post to your account after you spend $3,000 on purchases in the first 3 months from account opening.

Our notes: This is the highest point offering we’ve seen for this card. Previous high was 75,000 last December. As for other offers, it seems that every February there is an offer that includes a companion pass + about 30,000 points. The companion pass offer may be better than this one, depending on how much you’re able to use it.

Click for more details and booking links Southwest Rapid Rewards® Credit Cards: $400 statement credit and 40,000 Southwest Rapid Rewards after you spend $3,000 on purchases in the first 4 months from account opening.

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