Around the US 
in $60s-$260s RT
Good ol' reliable Southwest. They may have banished their free checked bag policy, but it's good to know that some things don't change.
Southwest has been going all in on Cyber Monday for years now, and this year we're seeing more of the same. Except now it's 50% off the base fares, so the flights are just that much cheaper! Kudos, Southwest!
As usual, they've got fares to every corner of the USA, from Portland, Maine to Portland, Oregon. We've collected some of the best ones for you, but you can take a look at this map to track down any specific routes you're looking for :-)
Taking off ✈️
Tip Published: Dec 01, 2025
Round trips from Atlanta (ATL):
- Bozeman (BZN) - $261
- Buffalo (BUF) - $148
- Denver (DEN) - $145 (non-stop)
- New York LaGuardia (LGA) - $92 (non-stop)
- Omaha (OMA) - $169
Round trips from Austin (AUS):
- Boston (BOS) - $149
- Bozeman (BZN) - $140
- Nashville (BNA) - $84 (non-stop)
- San Francisco (SFO) - $104 (non-stop)
Round trips from Baltimore (BWI):
- Seattle (SEA) - $115
Round trips from Boston (BOS):
- Austin (AUS) - $149
- Chicago Midway (MDW) - $79 (non-stop)
- Denver (DEN) - $104 (non-stop)
- Fort Lauderdale (FLL) - $105
- Nashville (BNA) - $84 (non-stop)
- New Orleans (MSY) - $119
- Portland (PDX) - $115
- San Diego (SAN) - $149
- Tampa (TPA) - $101
Round trips from Chicago Midway (MDW):
- Boston (BOS) - $79 (non-stop)
- Bozeman (BZN) - $135
- Los Angeles (LAX) - $144
- Phoenix (PHX) - $134 (non-stop)
- San Francisco (SFO) - $163
Round trips from Dallas (DAL):
- Detroit (DTW) - $148
- San Francisco (SFO) - $158
- Seattle (SEA) - $124
- Tulsa (TUL) - $97 (non-stop)
Round trips from Denver (DEN):
- Atlanta (ATL) - $145 (non-stop)
- Boston (BOS) - $104 (non-stop)
- Bozeman (BZN) - $120 (non-stop)
- San Diego (SAN) - $84 (non-stop)
Round trips from Fort Lauderdale (FLL):
- Boston (BOS) - $105
- Minneapolis (MSP) - $153
- Portland (PDX) - $130
Round trips from Houston (HOU):
- Boise (BOI) - $151
- Cleveland (CLE) - $150
- Des Moines (DSM) - $154
- Minneapolis (MSP) - $150
- Philadelphia (PHL) - $145
Round trips from Las Vegas (LAS):
- Bozeman (BZN) - $114
- Minneapolis (MSP) - $150
- Orlando (MCO) - $144 (non-stop)
- Seattle (SEA) - $64 (non-stop)
Round trips from Los Angeles (LAX):
- Boise (BOI) - $114
- Buffalo (BUF) - $122
- Chicago Midway (MDW) - $144
- Portland (PWM) - $151
- Washington Reagan (DCA) - $164
Round trips from Miami (MIA):
- Albuquerque (ABQ) - $181
- Portland (PWM) - $134
Round trips from New York LaGuardia (LGA):
- Albuquerque (ABQ) - $117
- Atlanta (ATL) - $92 (non-stop)
- New Orleans (MSY) - $94 (non-stop)
- Phoenix (PHX) - $129
- Salt Lake City (SLC) - $134
- San Francisco (SFO) - $121
- St Louis (STL) - $156 (non-stop)
Round trips from Orlando (MCO):
- Albuquerque (ABQ) - $248
- Las Vegas (LAS) - $144 (non-stop)
- Minneapolis (MSP) - $165
- Richmond (RIC) - $79 (non-stop)
- San Francisco (SFO) - $134
- Washington Reagan (DCA) - $72 (non-stop)
Round trips from Philadelphia (PHL):
- Albuquerque (ABQ) - $151
- Houston (HOU) - $145
- Omaha (OMA) - $153
- Seattle (SEA) - $154
Round trips from Phoenix (PHX):
- Charleston (CHS) - $147
- Chicago Midway (MDW) - $134 (non-stop)
- Milwaukee (MKE) - $126
- New York LaGuardia (LGA) - $129
- San Francisco (SFO) - $78 (non-stop)
Round trips from Portland (PDX):
- Albuquerque (ABQ) - $104
- Boston (BOS) - $115
- Fort Lauderdale (FLL) - $130
- Nashville (BNA) - $145
- New Orleans (MSY) - $139
- Salt Lake City (SLC) - $101
Round trips from Salt Lake City (SLC):
- Buffalo (BUF) - $179
- Louisville (SDF) - $174
- New York LaGuardia (LGA) - $134
- Portland (PDX) - $101
- San Diego (SAN) - $64 (non-stop)
Round trips from San Diego (SAN):
- Boston (BOS) - $149
- Bozeman (BZN) - $94
- Charleston (CHS) - $174
- Denver (DEN) - $84 (non-stop)
- Salt Lake City (SLC) - $64 (non-stop)
- Tulsa (TUL) - $142
Round trips from San Francisco (SFO):
- Austin (AUS) - $104 (non-stop)
- Charleston (CHS) - $151
- Chicago Midway (MDW) - $163
- Dallas (DAL) - $158
- New York LaGuardia (LGA) - $121
- Orlando (MCO) - $134
- Phoenix (PHX) - $78 (non-stop)
- San Antonio (SAT) - $160
- Spokane (GEG) - $101
Round trips from Seattle (SEA):
- Baltimore (BWI) - $115
- Cleveland (CLE) - $144
- Dallas (DAL) - $124
- Las Vegas (LAS) - $64 (non-stop)
- Omaha (OMA) - $114
- Philadelphia (PHL) - $154
Round trips from Tampa (TPA):
- Boston (BOS) - $101
- Bozeman (BZN) - $150
- El Paso (ELP) - $174
- Omaha (OMA) - $187
Round trips from Washington Reagan (DCA):
- Columbus (CMH) - $124 (non-stop)
- Kansas City (MCI) - $150 (non-stop)
- Los Angeles (LAX) - $164
- Orlando (MCO) - $72 (non-stop)
How to Book
This is a Takeoff-only Flight for Jack's Flight Club Takeoff members only. For step by step instructions on how to book it you'll need to login or upgrade to Takeoff membership.
