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

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Airfare Deals American Airlines Flights from Chicago / Milwaukee Kingston Oneworld

Most domestic carriers have round-trip flights to/from various destinations in the USA at a discount today for $78-$198, NONSTOP or with a connection. Dates vary, use the linked calendar. Cheapest fares are mostly midweek. Origin/Destination reversible. Excluding Frontier/Spirit.

Notes: Most fares are between January and March with some weekend availability.

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

If you like this style of report, it’s a subset of daily Patreon recap [link]. That recap is the unfiltered list of every fare that was priced below the 6-month moving average. If you’re interested, there is a free 7-day preview.

Click for more details and booking links Domestic Airfare Sale: to/from various domestic destinations $78-$198 r/t (see list on website) [most dates Jan-Mar] – United / jetBlue / Delta / American / Southwest / Alaska Airlines

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

American Airlines has round-trip flights from Chicago (ORD) to Grand Cayman (GCM) for $326-$333 with a connection. Flights January to May. Departures on Tuesday and Wednesday. Origin/Destination reversible.

Hopper has a Cyber Monday coupon for -$200 off Cayman Hotels.

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/from Grand Cayman $326-$333 r/t [January-May] (Use $200 off Cayman Hotels coupon) – American Airlines

Airfare Deals American Airlines Flights from Chicago / Milwaukee Grand Cayman Oneworld

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. 

Click for more details and booking links Recap: Southwest $500 gift-card for $399, Southwest 75,000 point, United 60,000 point, and Amazon Prime $200 gift-card welcome-offer / +25% Point transfer bonus for Air France, KLM, JetBlue via Chase / Hopper Coupons: $50 off Hyatt, $50 Fiji Airways, +more

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

Alaska Airlines has a Black Friday Buy One Get One deal (only pay + tax/fees on the additional fare). Use code: BFBOGO23. Deal is valid TODAY ONLY. Flights between January and March.

Discount code is valid for 50% off coach base fare levels published at alaskaair.com when two tickets are booked together. Valid for itineraries with a minimum and maximum of two people, traveling together and booked and ticketed at the same time in the same reservation and at the same fare; valid for one-way or round-trip travel.

More details are on the Alaska Airlines promo page [linked].

Click for more details and booking links Alaska Airlines: Black Friday – Buy One Get One: Mexico, Costa Rica, Belize, Guatemala, and The Bahamas [Jan-Mar] – Use code: BFBOGO23

Administrative Airfare Deals Alaska Airlines 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

Icelandair has round-trip flights from Chicago (ORD) to Dublin, Rome or Reykjavik (DUB, FCO, OSL, KEF) for $415-$448. Flights January to March. Extended weekends available.

Some small OTAs on Skyscanner and Google have this for about $386-$419; 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.

Flights to Reykjavik are NONSTOP. Other destinations have a connection.

Click for more details and booking links Cheap Flights: Chicago to Dublin, Rome, Oslo, or Reykjavik $386-$448 r/t [January-March] – Icelandair

Airfare Deals Dublin Flights from Chicago / Milwaukee IcelandAir

Scandinavian Airlines has round-trip flights from Chicago (ORD) to Stockholm, Manchester, Helsinki, Copenhagen, or Gothenburg (ARN, MAN, HEL, CPH, GOT) for $414-$448. Most flights are in April, except Copenhagen which has a range of December to April. Very few extended weekends available.

Stockholm and Copenhagen flights are NONSTOP. Other destinations have a connection.
Some small OTAs on Skyscanner and Google have this for about $394-$428; 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 Stockholm, Manchester, Helsinki, Copenhagen, or Gothenburg $394-$448 r/t [Apr / Dec-Apr] – Scandinavian Airlines

Airfare Deals Flights from Chicago / Milwaukee Scandinavian Airlines Stockholm

Alaska Airlines has round-trip flights from Chicago (ORD) to San Francisco (SFO) for $98-$118, NONSTOP. Flights November to February. Weekends available. Origin/Destination reversible. No Thanksgiving dates.

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: Chicago to/from San Francisco $98-$118 r/t [November-February] (No Thanksgiving) – Alaska Airlines

Airfare Deals Alaska Airlines Flights from Chicago / Milwaukee San Francisco

United has round-trip flights from Chicago (ORD) to Cozumel (CZM) for $254, NONSTOP. Flights November to January. Departures on Saturday. Origin/Destination reversible. 7-day minimum stay required. No Thanksgiving dates.

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 Cozumel $254 r/t [November-January] (No Thanksgiving) – United

Airfare Deals Cozumel Flights from Chicago / Milwaukee Star Alliance United

Chase has increased the sign-up bonus for the United℠ Explorer Card. It is now a 60,000 point bonus instead of 50,000. The bonus offer applies after spending $3,000 in the first 3-months of being approved for the card. This card has an annual fee of: $0 intro annual fee for the first year, then $95. We recommend this card for those of you who fly United because your first standard checked-bag for you and your companion is free, you get priority boarding, two United Club passes per year, and you get a 25% discount on inflight purchases on United-operated flights. 

The checked-bag perk will probably be the main draw for those of you who fly on the cheaper “Basic Economy” fares on United. Basic Economy fares on United don’t include a free checked-bag and this perk can save you from paying additional bag fees. 

Click for more details and booking links United℠ Explorer Card: Sign-up bonus increased to 60,000 United MileagePlus points

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