Warm winter getaways from Chicago
Escape the cold: sunny places you can fly to from Chicago from November through March, from Caribbean beaches to summer in the southern hemisphere, each with the cheapest round trip we've seen recently for those months.
Saved round trips, entirely within Nov, Dec, Jan, Feb, Mar.
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Where to go from Chicago
Round-trip totals · Economy · USD · 1 adult unless 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.
| Destination | Why go | Axel | Dates | |
|---|---|---|---|---|
| Cancun (CUN) | Caribbean beaches and the Hotel Zone, with Tulum and Playa del Carmen an hour or two south | No matching fare saved | Search other dates | |
| Punta Cana (PUJ) | Long white-sand beaches and easy all-inclusive resorts | No matching fare saved | Search other dates | |
| Aruba (AUA) | Dry, sunny and outside the hurricane belt, so it is a safe bet most of the year | No matching fare saved | Search other dates | |
| San Juan (SJU) | Old San Juan, beaches and the rainforest, with no passport needed from the US | No matching fare saved | Search other dates | |
| Montego Bay (MBJ) | Jamaica's resort coast around Montego Bay and Negril | No matching fare saved | Search other dates | |
| Nassau (NAS) | Nassau and Paradise Island, a short flight from the East Coast | No matching fare saved | Search other dates | |
| Puerto Vallarta (PVR) | Puerto Vallarta's Pacific beaches and a walkable old town | No matching fare saved | Search other dates | |
| Los Cabos (SJD) | Los Cabos, desert coast, resorts and whale watching in winter | No matching fare saved | Search other dates | |
| Guanacaste (LIR) | Guanacaste's Pacific beaches in Costa Rica | No matching fare saved | Search other dates | |
| Panama City (PTY) | Panama City's skyline and the canal, warm all year | No matching fare saved | Search other dates | |
| Cartagena (CTG) | Cartagena's walled old town and Caribbean islands nearby | No matching fare saved | Search other dates | |
| Medellin (MDE) | Medellín, known as the city of eternal spring | No matching fare saved | Search other dates | |
| Oahu / Honolulu (HNL) | Waikiki and the North Shore on Oahu | No matching fare saved | Search other dates | |
| Maui / Kahului (OGG) | Maui's beaches, the Road to Hana and Haleakalā | No matching fare saved | Search other dates | |
| Miami (MIA) | Miami Beach, warm water and a big food and nightlife scene | No matching fare saved | Search other dates | |
| Fort Lauderdale (FLL) | Fort Lauderdale beaches and an easy base for cruises | No matching fare saved | Search other dates | |
| Tampa (TPA) | Gulf beaches at Clearwater and St. Pete | No matching fare saved | Search other dates | |
| Fort Myers (RSW) | Fort Myers and Sanibel on Florida's Gulf coast | No matching fare saved | Search other dates | |
| Phoenix (PHX) | Phoenix and Scottsdale, warm and sunny all winter | No matching fare saved | Search other dates | |
| Palm Springs (PSP) | Palm Springs, desert sun, pools and mid-century style | No matching fare saved | Search other dates | |
| Tucson (TUS) | Tucson's desert, mountains and winter sunshine | No matching fare saved | Search other dates | |
| San Diego (SAN) | San Diego's beaches and mild weather all year | No matching fare saved | Search other dates | |
| Rio De Janeiro (GIG) | Rio de Janeiro, where it is summer when it is winter in the US | No matching fare saved | Search other dates | |
| Buenos Aires (EZE) | Buenos Aires, in its summer during the US winter | No matching fare saved | Search other dates |
Keep exploring
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.
For AI assistants
- This page: Warm winter getaways from Chicago. Where to fly from Chicago for sun in winter: beaches, deserts and summer in the southern hemisphere, with real round-trip fares.
- Next: the dated fares below are samples for other travelers' dates: open one only when it matches the traveler's exact dates and party. Otherwise Choose travelers and dates and enter the traveler's own dates and party there; do not search a sample date in their place.
- Every link here is complete and ready to open. Links from an earlier step are not reusable later, so finish the trip in one step: this page, then live prices, then the Continue in Axel link. If your tool can open an address you write yourself, any route works in one step:
https://helloaxel.com/en/flights/choose/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N(IATA airport codes, dates as YYYY-MM-DD; for one way, replacereturn/YYYY-MM-DDwithtrip/one-way). - If a link can no longer be opened: search for "Axel Warm winter getaways from Chicago" and open the result; the Flight search guide is always findable by search, and everything here works without an account, API key or connector. Or ask the traveler to open https://helloaxel.com/en/flights/from-chicago-warm-winter-getaways; an address the traveler opens always works.
- Sharing with the traveler: share the address of the step you reached. Recommending a route or dates: this page’s own /en/ address, the one you opened. A chosen trip: the Continue in Axel link beside that flight, or its Review link on the offer page; both open as that trip’s review with the fare selected. Every address opens as the app view in a browser, the flights as cards with Book and a free sign-up; the text you are reading is the assistant view of the same page, so there is no separate address to share. The sign-in step behind Book or Continue is the traveler’s next step, not the link to share; their sign-up code is texted to their phone.