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

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.

Current noteworthy mentions are:

(New!) Ends 08-07-24: United MileagePlus® Credit Cards: Welcome offers have increased by +10,000. Now earn between 30,000 to 90,000 points depending on the card.
(New!) Ends 06-17-24: Southwest Rapid Rewards Sale. Save 25% when booking with points. Fly between Jun-14 and Nov-20. Use code “SAVE25”.
(New!) Ends 07-31-24: 20% Air Canada transfer bonus. Get 20% bonus Aeroplan points when you transfer from Chase Ultimate Rewards points.

Click for more details and booking links Our updated list of coupon codes, discount codes, gift card discounts, and credit card bonuses as of 06/15/2024

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

These new offers are 10,000 more than what they were previously last month. Of these offerings, we think that the United Explorer Card has the best perk to annual fee ratio because we find a lot of value in being able to use it to book on United Basic Economy and get the free first bag perk with priority boarding. Those two perks alone negate a lot of the downside to basic economy.

Click for more details and booking links United MileagePlus® Credit Cards: Welcome offers have increased. Now earn between 30,000 to 90,000 points depending on the card. Offer expires 8/7/2024.

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

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.

Click for more details and booking links Cheap Flights: Chicago to London, United Kingdom $476-$500 r/t [September] – JetBlue

Airfare Deals Flights from Chicago / Milwaukee JetBlue London United Kingdom

(There are still several destinations that are priced below their moving averages. The Southwest Sale has ended, but you may be able to make use of these remaining fares on competing airlines.)

Most domestic carriers have round-trip flights to/from various destinations in the USA at a discount today for $67-$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.

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

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.

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.

Click for more details and booking links Domestic Airfare Sale: to/from various domestic destinations $67-$185 r/t (see list on website) [most dates Jul-Dec] – Southwest / United / Delta / American / 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

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.

Click for more details and booking links Nonstop Flights: Chicago to/from San Francisco, Salt Lake City, or San Diego $117-$144 r/t [August-December] (No Christmas) – United / American / Delta

Airfare Deals Flights from Chicago / Milwaukee San Francisco Star Alliance United

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.

Click for more details and booking links Nonstop Flights: Chicago to/from Austin, Tampa, Miami, San Antonio, Tampa, Nashville, or Philadelphia $75-$97 r/t [August-December] (No Christmas) – American Airlines / United / Southwest

Airfare Deals American Airlines Austin Flights from Chicago / Milwaukee Oneworld

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).

Click for more details and booking links Cheap Flights: Chicago to Amsterdam, Berlin, Manchester, or London $462-$517 r/t [September-April] – Icelandair

Airfare Deals Amsterdam Flights from Chicago / Milwaukee IcelandAir

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.

Click for more details and booking links Nonstop Flights: Chicago to/from San Francisco or Las Vegas $38-$45 r/t [August-October] (budget carrier) – Frontier

Airfare Deals Flights from Chicago / Milwaukee Frontier San Francisco

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).

Click for more details and booking links Nonstop Flights: Chicago to/from Cancun, Tulum, or San Jose del Cabo $223-$314 r/t [September-December] (No Christmas) – United

Airfare Deals Cancun Flights from Chicago / Milwaukee Star Alliance United

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.

Click for more details and booking links Nonstop Flights: Chicago to/from Nassau, Bahamas or Providenciales, Turks & Caicos Islands $288-$322 r/t [August-December] (No Christmas) – American Airlines

Airfare Deals American Airlines Flights from Chicago / Milwaukee Oneworld Providenciales Turks & Caicos Islands

Image Credits: Public Domain

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.

Click for more details and booking links Nonstop Flights: Chicago to/from Puerto Vallarta or Montego Bay, Jamaica $293-$330 r/t [Nov-Dec, Aug, Nov-Dec] (No Christmas / Thanksgiving) – American Airlines

Airfare Deals American Airlines Flights from Chicago / Milwaukee Oneworld Puerto Vallarta

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.

Click for more details and booking links Nonstop Flights: Chicago to/from St. Louis, Salt Lake City, Sacramento, San Antonio, San Jose, CA, or Rochester, NY $105-$142 r/t [August-December] (Weekends available) – United / Southwest

Airfare Deals Flights from Chicago / Milwaukee St. Louis Star Alliance United

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.

Click for more details and booking links Cheap Flights: Milwaukee to/from San Jose, Costa Rica $316-$331 r/t [Oct-Nov, Jan-Feb] (No Thanksgiving) – Delta

Airfare Deals Costa Rica Delta Flights from Chicago / Milwaukee Flights from Milwaukee San Jose SkyTeam

Amex has recently increased the welcome offer for several of the co-branded Delta SkyMiles.

Here is the list of the current offers:

Delta SkyMiles® Gold: 65,000 Bonus Miles after you spend $3,000 in purchases on your new card in your first 6 months of card membership.
Delta SkyMiles® Platinum: 85,000 Bonus Miles after you spend $4,000 in purchases on your new card in your first 6 months of card membership.
Delta SkyMiles® Reserve: 95,000 Bonus Miles after you spend $6,000 in purchases on your new card in your first 6 months of card membership.

Click for more details and booking links Delta SkyMiles® Credit Cards: Welcome offers have increased. Offer expires 7/17/2024.

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

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.

Click for more details and booking links Nonstop Flights: Chicago to/from Miami $137 r/t [August-November] (No Thanksgiving) – American Airlines / Southwest

Airfare Deals American Airlines Flights from Chicago / Milwaukee Miami Oneworld Southwest

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: New 85,000 Southwest Rapid Rewards bonus-offer after you spend $3,000 on purchases in the first 3 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

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.

Click for more details and booking links Nonstop Flights: Chicago to/from Seattle or Portland $149-$190 r/t [Aug-Apr / Aug-Nov] – United / American

Airfare Deals Flights from Chicago / Milwaukee Seattle Star Alliance United

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.

Click for more details and booking links Nonstop Flights: Chicago to/from Atlanta $38-$48 r/t [July-November] (No Thanksgiving) – Frontier

Airfare Deals Atlanta Flights from Atlanta Flights from Chicago / Milwaukee Frontier

Various carriers has round-trip flights to/from Europe at a discount today for $377-$560, 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.

Click for more details and booking links European Airfare Sale: to/from various European destinations $351-$560 r/t [dates vary, use calendar link] – Delta / United / TAP / Norse / ITA / Aer Lingus / British Airways

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

American Airlines, British Airways, and Iberia have round-trip flights from Chicago (ORD) to Porto (OPO) for $493-$509 with a connection. Flights in November, January, February, and March. Departures on Monday, Tuesday, Wednesday, and Sunday. 7-day minimum stay required. 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.

Click for more details and booking links Cheap Flights: Chicago to Porto, Portugal $493-$509 r/t [Nov, Jan-Mar] (No Thanksgiving) – American Airlines / British Airways / Iberia

Airfare Deals American Airlines British Airways Finnair Flights from Chicago / Milwaukee Oneworld Porto