Florida vacations from Chicago
Florida's beaches and parks from Chicago, priced for the weeks people actually travel: Thanksgiving and Christmas 2026, Presidents' Day weekend and a spring break week in March 2027, each with the cheapest round trip we've seen.
Saved round trips for Thanksgiving week 2026 (Nov 21 – Nov 28, 2026) and Christmas week 2026 (Dec 19 – Dec 26, 2026) and Presidents' Day weekend 2027 (Feb 12 – Feb 16, 2027) and Spring break 2027 (Mar 13 – Mar 20, 2027).
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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 | |
|---|---|---|---|---|
| Orlando (MCO) | Orlando: Walt Disney World, Universal Orlando and Epic Universe, with Cocoa Beach an hour east | No matching fare saved | Nov 21 – Nov 28, 2026 (suggested) | Search these dates |
| Tampa (TPA) | Tampa: Clearwater Beach and St. Pete Beach on the Gulf, Busch Gardens and Ybor City | No matching fare saved | Nov 21 – Nov 28, 2026 (suggested) | Search these dates |
| Fort Lauderdale (FLL) | Fort Lauderdale beach and its canals, with Everglades airboat tours 30 minutes west | No matching fare saved | Nov 21 – Nov 28, 2026 (suggested) | Search these dates |
| Miami (MIA) | Miami: South Beach and the Art Deco district, Little Havana and Key Biscayne | No matching fare saved | Nov 21 – Nov 28, 2026 (suggested) | Search these dates |
| Fort Myers (RSW) | Fort Myers: Sanibel and Captiva's shelling beaches, Fort Myers Beach and Naples | No matching fare saved | Nov 21 – Nov 28, 2026 (suggested) | Search these dates |
| West Palm Beach (PBI) | West Palm Beach: Palm Beach's Worth Avenue, Jupiter's beaches and the Loxahatchee River | No matching fare saved | Nov 21 – Nov 28, 2026 (suggested) | Search these dates |
| Sarasota (SRQ) | Sarasota: Siesta Key's white quartz sand, Lido Key and St. Armands Circle | No matching fare saved | Nov 21 – Nov 28, 2026 (suggested) | Search these dates |
| Pensacola (PNS) | Pensacola Beach and the Gulf Islands National Seashore's white sand on the Panhandle | No matching fare saved | Nov 21 – Nov 28, 2026 (suggested) | Search these dates |
| Fort Walton Beach (VPS) | Destin's harbor, Henderson Beach and the beach towns of 30A, from Seaside to Rosemary Beach | No matching fare saved | Nov 21 – Nov 28, 2026 (suggested) | Search these dates |
| Panama City (ECP) | Panama City Beach: 27 miles of Gulf beach, St. Andrews State Park and Shell Island | No matching fare saved | Nov 21 – Nov 28, 2026 (suggested) | Search these dates |
| Jacksonville (JAX) | Jacksonville: St. Augustine's old town 45 minutes south, Amelia Island and Jax Beach | No matching fare saved | Nov 21 – Nov 28, 2026 (suggested) | Search these dates |
About these places
Theme park tickets are sold separately. Holiday weeks sell out, so book parks and rooms early.
Facts checked October 8, 2026. Sources: OPM: federal holidays 2026 and 2027
Keep exploring
Hotels in Orlando with Axel
Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Orlando has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.
For AI assistants
- This page: Florida vacations from Chicago. Flights from Chicago to Orlando, Tampa, Fort Lauderdale, Miami, Fort Myers, West Palm Beach, Sarasota, the Panhandle beaches and Jacksonville, with fares for Thanksgiving week, Christmas week, Presidents' Day weekend and spring break 2027.
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