Search 86 Chicago to Cabo San Lucas Resort Vacation Deals and 31 Resorts

At CheapCaribbean.com, we’ve created 86 custom vacation packages for 31 different resorts in Cabo San Lucas. Each “Flight + Hotel” package is priced per person. Each “Hotel Only” package is priced per night. Make sure to use the filters to find the perfect Cabo San Lucas resort deal for you!
× Amenities
× Class
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FLIGHT + HOTEL
Grand Velas Los Cabos - All Inclusive Cabo San Lucas
All-Inclusive
2 Deals Available!
From $2,334 to $3,613* /person
3 to 5 Day Trips - Aug to Nov
FLIGHT + HOTEL
The Residences at Hacienda Encantada Cabo San Lucas
2 Deals Available!
From $1,825 to $2,609* /person
3 to 5 Day Trips - Aug to Nov
FLIGHT + HOTEL
Nobu Hotel Los Cabos - European Plan Cabo San Lucas
2 Deals Available!
From $1,033 to $1,441* /person
3 to 5 Day Trips - Aug to Nov
FLIGHT + HOTEL
Grand Fiesta Americana Los Cabos  All Inclusive Golf & Spa Cabo San Lucas
All-Inclusive
2 Deals Available!
From $936 to $1,304* /person
3 to 5 Day Trips - Aug to Nov
FLIGHT + HOTEL
Breathless Cabo San Lucas Resort & Spa - All Inclusive Cabo San Lucas
All-Inclusive
2 Deals Available!
From $910 to $1,335* /person
3 to 5 Day Trips - Aug to Nov
FLIGHT + HOTEL
Riu Palace Baja California - All Inclusive Cabo San Lucas
All-Inclusive
2 Deals Available!
From $843 to $1,126* /person
3 to 5 Day Trips - Aug to Nov
FLIGHT + HOTEL
Riu Palace Cabo San Lucas - All Inclusive Cabo San Lucas
All-Inclusive
2 Deals Available!
From $808 to $1,057* /person
3 to 5 Day Trips - Aug to Nov
FLIGHT + HOTEL
Casa Dorada Los Cabos Resort & Spa Cabo San Lucas
2 Deals Available!
From $779 to $918* /person
3 to 5 Day Trips - Aug to Nov
HOTEL ONLY
Waldorf Astoria Los Cabos Pedregal Cabo San Lucas
3 Deals Available!
From $746 to $2,595* /person
1 to 5 Day Trips - Jul to Oct
FLIGHT + HOTEL
Riu Santa Fe - All Inclusive Cabo San Lucas
All-Inclusive
2 Deals Available!
From $705 to $886* /person
3 to 5 Day Trips - Aug to Nov

Chicago to Cabo San Lucas Resort Vacation Packages

Escape the ordinary and embark on an extraordinary journey from Chicago to Cabo San Lucas with CheapCaribbean.com's vacation packages. We collaborate with top hotels including Grand Fiesta Americana Los Cabos All Inclusive Golf & Spa, Grand Velas Los Cabos - All Inclusive and Hacienda Encantada Resort & Residences - All Inclusive - all offering packages for travelers flying from ORD airport to SJD, and providing you with an array of options from our wide selection of hotels in Cabo San Lucas. Enjoy premium amenities such as an exercise gym, a tour/sightseeing desk and a spa tailored to enrich your holiday experience. Our packages are comprehensive, enabling you to immerse in Cabo San Lucas's rich culture, explore its must-see attractions and enjoy its agreeable weather, making your vacation truly memorable.

If you’re flying from Chicago, then we’ve got some enticing deals that come in varied durations, be it a 3-day and 5-day retreat. Starting from an attractive $677 per person, these deals encompass not just your flight but also a luxurious stay in some of the top-rated hotel brands in Cabo San Lucas. As of 08-29-2024 we have 94 curated deals available, ranging from the most budget-friendly options to premium experiences, so there's a perfect fit for everyone. Of the hotels that currently offer great deals, we have special deals for various types of hotel experiences:*

• Romantic: $936 per person for a 3-night stay at Grand Fiesta Americana Los Cabos All Inclusive Golf & Spa flying from ORD airport (Nov 19 - Nov 21, 2024)
• Family-Friendly: $705 per person for a 3-night stay at Riu Santa Fe - All Inclusive flying from ORD airport (Nov 19 - Nov 21, 2024)
• Luxury: $3,613 per person for a 5-night stay at Grand Velas Los Cabos - All Inclusive flying from ORD airport (Nov 19 - Nov 23, 2024)
• All-Inclusive: $936 per person for a 3-night stay at Grand Fiesta Americana Los Cabos All Inclusive Golf & Spa flying from ORD airport (Nov 19 - Nov 21, 2024)
• Adults-Only: $910 per person for a 3-night stay at Breathless Cabo San Lucas Resort & Spa - All Inclusive flying from ORD airport (Nov 19 - Nov 21, 2024)

Find Vacation Packages to Cabo San Lucas by Length of Stay

3-Day Vacation Packages from Chicago to Cabo San Lucas

Embark on a quick, refreshing break from the everyday routine with CheapCaribbean.com's current 3-day vacation packages from Chicago to the exquisite Cabo San Lucas. With 33 meticulously curated deals on offer as of 08-29-2024, you can enjoy the best of both worlds - fantastic value and unforgettable experiences. Each deal, priced per person, covers your flight and accommodation costs, allowing you to stay at renowned hotel like Grand Fiesta Americana Los Cabos All Inclusive Golf & Spa, Grand Velas Los Cabos - All Inclusive and Hacienda Encantada Resort & Residences - All Inclusive. With an average price per person starting from just $809 per person, and a spectrum of deals ranging from the $677 to more luxurious $2,334 per person, every traveler can find their perfect getaway. Check these popular 3-day packages to Cabo San Lucas...*

5-Day Vacation Packages from Chicago to Cabo San Lucas

Dive deeper into your vacation dreams with CheapCaribbean.com's 5-day vacation packages, offering an extended escape from Chicago to the captivating Cabo San Lucas. With 33 specially tailored deals available right now, we provide an unbeatable combination of excellent value and extraordinary experiences. Each package, thoughtfully priced per person, includes both flight and accommodation costs at top-tier hotels such as The Residences at Hacienda Encantada, Grand Velas Los Cabos - All Inclusive and Nobu Hotel Los Cabos - European Plan. With an average price per person of $1,257, and an array of offers spanning budget-friendly deals like $866 per person to luxury options such as $3,613, there's a perfect fit for every explorer. Discover these popular 5-day packages to Cabo San Lucas...*

Map of Cabo San Lucas Resorts

Chicago to Cabo San Lucas Vacation Package FAQs

What resort brands offer vacations to Cabo San Lucas from Chicago?

Independent, Riu Resorts, Preferred, Hyatt Inclusive Collection and Fiesta Americana Hotels & Resorts currently all have amazing package deals on flights from Chicago to Cabo San Lucas with resort accommodations included. Here are some of their best deals as of 08-29-2024:

What all-Inclusive resorts should I look at in Cabo San Lucas?

If you want all your flights, hotel, food and drinks covered in one simple deal, then as of 08-29-2024 look no further than the Riu Santa Fe - All Inclusive which is offering a 3-day stay at their amazing resort for $705 per person, the Riu Palace Cabo San Lucas - All Inclusive with a 5-day stay for only $1,057 per person, and Riu Palace Baja California - All Inclusive at $1,126 per person for a 5-day all-inclusive vacation - all flying from Chicago!

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*Current vacation package prices are listed as of 08-29-2024 and are subject to change based on dates, origins and availability.