All-inclusive resort weeks from Chicago

All-inclusive weeks from Chicago, priced for two adults: fares for a week starting January 16, February 13 or March 6, 2027, to the resort zones where the hotel covers meals and drinks. The February week covers Presidents' Day weekend.

Saved round trips for 6–8 nights, entirely within Jan, Feb, Mar.

Cheapest right now: Puerto Vallarta $297 · San Jose Cabo $301 · Cancun $390

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Flights from Chicago

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All-inclusive resort weeks from other cities

Fares observed October 7 – 9, 2026. USD for the travelers shown. Search a trip for current prices.

Where to go from Chicago

Round-trip totals · Economy · USD · 2 adults (the whole party) where saved, else the party shown. "From" is a starting total: you pick the return in Axel. Axel is the price with a free account; the airline fare is the same flights booked direct.

DestinationWhy goAxelDates
Cancun (CUN)Cancún's Hotel Zone and the Riviera Maya resorts from Playa del Carmen down to Tulum$390 (airline $411) · 1 adultMar 13–20, 2027Check prices
Punta Cana (PUJ)Punta Cana's Bávaro beach, lined with all-inclusive resorts, 20 minutes from the airport$599 (airline $632) · 1 adultMar 13–20, 2027Check prices
Montego Bay (MBJ)Montego Bay's resort strip and Negril's Seven Mile Beach, 90 minutes west$768 (airline $813) · 1 adultMar 13–20, 2027Check prices
Puerto Vallarta (PVR)Nuevo Vallarta and the Riviera Nayarit resorts north of the airport, with Puerto Vallarta's old town nearby$297 (airline $313) · 1 adultMar 13–20, 2027Check prices
Los Cabos (SJD)The Los Cabos corridor between San José del Cabo and Cabo San Lucas, with Medano Beach for swimming$301 (airline $318) · 1 adultMar 13–20, 2027Check prices
Guanacaste (LIR)Guanacaste's Papagayo peninsula resorts and the beaches at Tamarindo and Playa Conchal$829 (airline $875) · 1 adultMar 13–20, 2027Check prices
Aruba (AUA)Aruba's Palm Beach high-rise resorts and Eagle Beach, with calm water and steady trade windsfrom $693 (airline $732) · 1 adultMar 18–26, 2027Check prices
Nassau (NAS)Nassau's Cable Beach resorts and Paradise Island, 15 minutes from the airport$650 (airline $686) · 1 adultMar 13–20, 2027Check prices
Sint Maarten (SXM)St. Maarten's Maho and Orient Bay resorts, with the famous beach landings right by the airportNo matching fare savedJan 16 – Jan 23, 2027 (suggested)Search these dates
Huatulco (HUX)Huatulco's nine bays, with resorts on Tangolunda Bay and quieter beaches at La Entrega and Santa CruzNo matching fare savedJan 16 – Jan 23, 2027 (suggested)Search these dates
Ixtapa/Zihuatanejo (ZIH)Ixtapa's resort beach, Playa El Palmar, with Zihuatanejo's fishing village and Playa La Ropa next doorNo matching fare savedJan 16 – Jan 23, 2027 (suggested)Search these dates

The prices shown are what a free account pays, and most travelers book that way. Membership is optional and takes the same flights lower. Live search shows the same free-account price.

About these places

Fares cover flights for two adults; the resort is booked separately. Check entry rules for your passport before you book.

Facts checked October 8, 2026. Sources: OPM: federal holidays 2026 and 2027 · Surrey County Council: term dates 2026 to 2027 (February half-term 15 to 19 February 2027)

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Hotels in Cancun with Axel

Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Cancun has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.

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  • This page: All-inclusive resort weeks from Chicago. Flights from Chicago to the all-inclusive resort zones: Cancún and the Riviera Maya, Punta Cana, Montego Bay, Puerto Vallarta, Los Cabos, Guanacaste, Aruba, Nassau, St. Maarten, Huatulco and Ixtapa, priced for two adults for a week in January, February or March 2027.
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