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

Amex has recently increased the welcome offer for the Marriott Bonvoy Business® American Express® Card to 5 Free Night Awards after spending $8,000 in the first 6-months of card membership. The previous offer was 3 nights. Each bonus Free Night Award has a max redemption value of 50,000 Marriott Bonvoy Points. Which means that if you maximize where you stay, this welcome bonus is equivalent to 250,000 Marriott Bonvoy Points. Resort fees & terms apply.

This card has an annual fee of $125 so we can only recommend this card if you’re a Marriott loyalist that can utilize the card perks enough to offset the annual fee. 

Click for more details and booking links Marriott Bonvoy Business® American Express® Card: Welcome offer increased to 5 Free Night Awards after spending $8,000 in the first 6-months of card membership (offer ends Jul-10)

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 United have round-trip flights from Chicago (ORD) to Nashville (BNA) for $97-$118, NONSTOP. Flights June to November. No Thursday 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 Nashville $97-$118 r/t [June-November] (No Thanksgiving) – American Airlines / United

Airfare Deals American Airlines Flights from Chicago / Milwaukee Nashville Oneworld 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.

Current standout offers are:

The Chase Sapphire Preferred/Reserve has a new 75,000 Ultimate Rewards points sign-up offer.
Southwest flights are now bookable via the Chase Travel Portal and Google Flights.
Southwest is offering a limited time Companion Pass (which is valid 39-days, starting on October-5th) if you book a flight to Hawaii in the next 2-days.
Hyatt is offering 20% off Europe, Africa and the Middle East Hotels (registration required).
Amex is offering $50 off when you spend $250 at Grand Hyatt (registration required).
Hopper offers the following coupons: $100 off Singapore Airlines flights to Singapore, $50 Air New Zealand, $100 off Fiji Airways. $50 off Royal Air Maroc flights, $50 off Air India flights.

Click for more details and booking links Our updated list of coupon codes, discount codes, gift card discounts, and credit card bonuses as of 05/22/2024

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

Airfare Deals American Airlines Boston Flights from Chicago / Milwaukee Oneworld Star Alliance United

American Airlines and Delta have round-trip flights from Milwaukee (MKE) to Nassau, Bahamas, Montego Bay, or Aruba (NAS, MBJ, AUA) for $302-$377 with a connection. Flights August to November. Very few weekends available. Origin/Destination reversible. No Thanksgiving dates.

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.

Click for more details and booking links Cheap Flights: Milwaukee to/from Nassau, Bahamas, Montego Bay, or Aruba $302-$377 r/t [August-November] (No Thanksgiving) – American Airlines / Delta

Airfare Deals American Airlines Bahamas Delta Flights from Chicago / Milwaukee Flights from Milwaukee Nassau Oneworld SkyTeam

JetBlue and Delta have round-trip flights from Chicago (ORD/MDW) to Nassau, Bahamas (NAS) for $332-$351 with a connection. Flights May, June, August, September, October, and November. Weekends available. 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: Chicago to/from Nassau, Bahamas $332-$351 r/t [May, Jun, Aug-Nov] (No Thanksgiving) – JetBlue / Delta

Airfare Deals Bahamas Delta Flights from Chicago / Milwaukee JetBlue Nassau SkyTeam

American Airlines has round-trip flights from Chicago (ORD) to San Jose del Cabo, Puerto Vallarta, or Montego Bay (SJD, PVR, MBJ) for $336, NONSTOP. Flights in August, October, and November. Departures on Monday, Tuesday, and Saturday. 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 San Jose del Cabo, Puerto Vallarta, or Montego Bay $333-$376 r/t [Aug, Oct, Nov] (No Thanksgiving) – American Airlines

Airfare Deals American Airlines Flights from Chicago / Milwaukee Oneworld San Jose del Cabo

Delta has round-trip flights from Chicago (ORD) to Kahului (OGG) for $342 with a connection. Flights September to November. Departures on Monday, Tuesday, Wednesday, 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: Chicago to/from Maui-Kahului, Hawaii $342 r/t [September-November] (No Thanksgiving) – Delta

Airfare Deals Delta Flights from Chicago / Milwaukee Kahului SkyTeam

Scandinavian Airlines has round-trip flights from Chicago (ORD) to London or Hamburg (LHR,HAM) for $449-$474 with a connection. London Flights in November, January, February, and March. Hamburg Flights in November and January. No Thanksgiving dates.

Some small OTAs on Skyscanner and Google have this for as low as $415; 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 London or Hamburg $415-$449 r/t [dates vary] (No Thanksgiving) – Scandinavian Airlines

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

Scandinavian Airlines has round-trip flights from Chicago (ORD) to Amsterdam, Gdansk, Helsinki, Milan, Malaga, Oslo, or Copenhagen (AMS, GDN, HEL, MXP, AGP, OSL, CPH) for $390-$399 with a connection. Flights November to March. No Thanksgiving dates.

Malaga fares are only in November.

Some small OTAs on Skyscanner and Google have this for as low as $362; 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, Gdansk, Helsinki, Milan, Malaga, Oslo, or Copenhagen $362-$399 r/t [November-March] (No Thanksgiving) – Scandinavian Airlines

Airfare Deals Amsterdam Flights from Chicago / Milwaukee Scandinavian Airlines

American Airlines has round-trip flights from Chicago (ORD) to Philadelphia (PHL) for $117-$125, NONSTOP. Flights May to September. No Friday departures. Extended weekends available. Origin/Destination reversible.

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 Philadelphia $117-$125 r/t [May-September] – American Airlines

Airfare Deals American Airlines Flights from Chicago / Milwaukee Oneworld Philadelphia

American Airlines and United have round-trip flights from Chicago (ORD) to Dallas (DFW) for $137-$164, NONSTOP. Flights May to September. Extended weekends available. Origin/Destination reversible.

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 Dallas $137-$164 r/t [May-September] – American Airlines / United

Airfare Deals American Airlines Dallas Flights from Chicago / Milwaukee Oneworld Star Alliance United

Aer Lingus Airfare Deals Flights from Chicago / Milwaukee Manchester

Tap Air Portugal and Aer Lingus have round-trip flights from Chicago (ORD) to Lisbon (LIS) for $499-$504, NONSTOP or with connections. Flights September to March. 7-day minimum stay required.

Some small OTAs on Skyscanner and Google have this for about $478; 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.

Click for more details and booking links Nonstop Flights: Chicago to Lisbon $478-$504 r/t [September-March] – Tap Air Portugal / Aer Lingus

Aer Lingus Airfare Deals Flights from Chicago / Milwaukee Lisbon TAP Air Portugal

[05/14/2024 @ 01:44 PM CT] This fare is probably dead. We are no longer seeing valid fares on Air France/Delta. Congrats to those of you who were able to pick it up within the short window of time it was available.
The fastest way to be informed of new fare sales is to join our Telegram Channel (link).

Delta and Air France have round-trip flights from Chicago (ORD) to Dublin or Cork, Ireland (DUB, ORK) for $201-$378 with a connection. Flights September to October. Extended weekends available.

Cork flight has long connection times.

Click for more details and booking links Cheap Flights: Chicago to Dublin or Cork, Ireland $201-$378 r/t [September-October] – Delta / Air France

Airfare Deals Delta Dublin Flights from Chicago / Milwaukee SkyTeam

Airfare Deals Calgary Flights from Chicago / Milwaukee WestJet

Various carriers has round-trip flights to/from Europe at a discount today for $280-$579, NONSTOP or with a connection (see list on our website). Dates vary, use the calendar link in the post.

This list includes several most discount LCC carriers. Those carriers may have additional fees for bags, seat, and meals.
Denver doesn’t have any North African deals in this list. Only New York and Chicago do: Casablanca or Marrakesh.

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: New York/Newark, Denver, or Chicago to/from various European and North African destinations $351-$525 r/t [dates vary, use calendar link] – United / TAP / Norse / ITA / Delta / Aer Lingus / British Airways

Aer Lingus Airfare Deals Alaska Airlines Delta Flights from Chicago / Milwaukee Flights from Denver Flights from New York San Francisco SkyTeam Star Alliance United

Airfare Deals Delta Flights from Chicago / Milwaukee Paris SkyTeam

Image Credits: Katie Haugland Bowen

United has round-trip flights from Chicago (ORD) to Houston (IAH) for $137-$143, NONSTOP. Flights June to August. No Sunday departures. 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).

Click for more details and booking links Nonstop Flights: Chicago to/from Houston $137-$143 r/t [June-August] – United

Airfare Deals Flights from Chicago / Milwaukee Houston Star Alliance United

American Airlines, British Airways, and Finnair have round-trip flights from Chicago (ORD) to Palma, Mallorca (PMI) for $505 with a connection. Flights November to March. Departures on Monday, Tuesday, Wednesday, and Sunday. No Thanksgiving dates.

A -$40 price drop from when we mentioned this a few days ago.

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 Palma, Mallorca (Balearic Islands) $505 r/t [November-March] (No Thanksgiving) – American Airlines / British Airways / Finnair

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