Bundle Southwest® flight + hotel and save big on your next vacation package. Our goal is to provide you with a superb vacation experience from beginning to end. We appreciate the uniqueness of our customers. No two people are alike, so no two vacations should be alike. With Southwest Vacations, you can customize your vacation package to fit your needs and wants.
Chicago
Cancun - Riviera Maya Hotels
Montego Bay
Save up to 40%
Punta Cana
Save up to 50%
Montego Bay
Complimentary tours
Cancun - Cancun / Riviera Maya
Up to $600 in resort coupons
*$75 per-reservation promotion code savings apply on flight + hotel vacation packages of $500 or more to any domestic destination we offer. Savings are reflected in the package price when using promotion code SEMIANNUAL125 at the time of booking. $100 per-reservation promotion code savings apply on flight + hotel vacation packages of $1,000 or more to any domestic destination we offer. Savings are reflected in the package price when using promotion code SEMIANNUAL125 at the time of booking. $125 per-reservation promotion code savings apply on flight + hotel vacation packages of $1,500 or more to any domestic destination we offer. Savings are reflected in the package price when using promotion code SEMIANNUAL125 at the time of booking. $150 per-reservation promotion code savings apply on flight + hotel vacation packages of $500 or more to any international or Hawaii destination we offer. Savings are reflected in the package price when using promotion code SEMIANNUAL250 at the time of booking. $200 per-reservation promotion code savings apply on flight + hotel vacation packages of $1,000 or more to any international or Hawaii destination we offer. Savings are reflected in the package price when using promotion code SEMIANNUAL250 at the time of booking. $250 per-reservation promotion code savings apply on flight + hotel packages of $1,500 or more to any international or Hawaii destination we offer. Savings are reflected in the package price when using promotion code SEMIANNUAL250 at the time of booking. Length of stay for flight and hotel components must match. Promotion code intended for redemption by individual consumer only. One-day advance purchase is required. Restrictions, exclusions, and blackout dates may apply to hotel offers. Savings valid if booked 3/5/2024–4/1/2024 by 6:00 p.m. CT for travel 3/6/2024–11/2/2024.
**Get $100 off in instant savings when you book a flight + hotel package to any Hawaii destination we offer. Five-night stay required. Instant savings will be applied to the price of your vacation at checkout. If you change or modify your reservation after time of booking, you may no longer be eligible for the savings. One-day advance purchase is required. Restrictions, exclusions, and blackout dates may apply to hotel offers. Savings valid if booked 3/18/2024–3/22/2024 by 6:00 p.m. CT for travel 3/19/2024–11/2/2024.
***One-day advance purchase is required. 5,000 Rapid Rewards® bonus points will be awarded to each Member on flight + hotel vacation packages of three nights or more at any RIU Hotels & Resorts property in Mexico, Central America, and the Caribbean. To earn Rapid Rewards points for a vacation package, enter each Passenger's Rapid Rewards account number during checkout. Rapid Rewards account numbers can also be entered by visiting your account at Southwest.com®, when you check in online for your flight, or by providing your account number at the airport counter or gate before boarding your flight. Please allow up to eight weeks after completed qualifying travel for the 5,000 Rapid Rewards bonus points to be posted to each Member on the reservation with a Rapid Rewards account number at time of booking. Rapid Rewards points are awarded in addition to the base Rapid Rewards points for air offered with any package purchase and indicated during the booking process and on travel documents. Points do not count towards A-List or A-List Preferred status. Points will be rewarded if booked 3/5/2024–4/1/2024 by 6:00 p.m. CT for travel 3/6/2024–11/2/2024. All Rapid Rewards rules and regulations apply and can be found at Southwest.com/rrterms.
^Five-night minimum stay required. Instant savings vary by resort. Get up to $200 in instant savings at select Iberostar Hotels and Resorts. Get up to $250 in instant savings at select Iberostar Selection Hotels and Resorts. Get up to $300 in instant savings at select Iberostar Coral Level Hotels and Resorts. Get up to $400 in instant savings at select Iberostar Grand Hotels and Resorts. Reservation includes instant savings that have been applied to the pricing of your vacation. If you change or modify your reservation after the time of booking, you may no longer be eligible for the savings. One-day advance purchase is required. Restrictions, exclusions, and blackout dates may apply to hotel offers. Savings valid if booked 3/1/2024–3/31/2024 by 6:00 p.m. CT for travel 3/2/2024–11/2/2024.
†First and second checked bags. Weight and size limits apply. A golf bag can be substituted for one checked bag.