Valentine's Day getaways from Chicago
Valentine's Day 2027 is a Sunday, the day before Presidents' Day, so it makes a long weekend. Fares from Chicago for Friday, February 12 to Monday, February 15, for romantic cities, wine country and warm beaches.
Saved round trips for Valentine's Day weekend 2027 (Feb 12 – Feb 15, 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 | |
|---|---|---|---|---|
| Paris (CDG) | Evening walks along the Seine, dinner in the Marais and the view from Montmartre | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
| Venice (VCE) | Gondola rides through quiet back canals and winter evenings on St. Mark's Square | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
| Rome (FCO) | Candlelit trattorias in Trastevere and the Trevi Fountain late at night | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
| Charleston (CHS) | Carriage rides past Rainbow Row and the Battery, and Lowcountry dinners downtown | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
| Santa Rosa (STS) | Sonoma and Napa wineries and country inns, a short drive from the Santa Rosa airport | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
| Savannah (SAV) | Moss-draped squares, Forsyth Park and riverfront inns in the historic district | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
| New Orleans (MSY) | Jazz clubs on Frenchmen Street and long dinners in the French Quarter | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
| Los Cabos (SJD) | Sunset sails past the Arch at Land's End and resorts along the Tourist Corridor | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
| Saint Lucia (UVF) | Resorts facing the twin Pitons near Soufrière, and a dip in the volcanic mud baths | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
| Maui / Kahului (OGG) | Whale-watching season off Maui and sunrise above the clouds at Haleakalā | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
| TULUM (TQO) | Beachfront cabanas below the Tulum ruins and swims in the cenotes nearby | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
| Phoenix (PHX) | Sedona's red rocks and spa resorts, about two hours' drive north of Phoenix | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
| Quebec (YQB) | Old Quebec's snowy stone streets and the Château Frontenac above the St. Lawrence | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
| Thira (JTR) | Caldera sunsets from Oia and Imerovigli, with the island quiet in the off-season | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
| Monterey (MRY) | Carmel-by-the-Sea's cottages and the Big Sur coast drive south of Monterey | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
| Santa Barbara (SBA) | Santa Ynez Valley wine tasting and a Spanish-style downtown by the beach | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
| Aspen (ASE) | Ski days on Aspen Mountain and fireside dinners in the old mining town | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
| Reykjavik (KEF) | Northern lights tours and the Blue Lagoon's warm water, close to Keflavík airport | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
About these places
Facts checked October 7, 2026. Sources: OPM: 2027 federal holidays (Washington's Birthday, Feb 15)
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Hotels in Paris with Axel
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For AI assistants
- This page: Valentine's Day getaways from Chicago. Valentine's Day 2027 getaways from Chicago: Paris, Venice, Rome, Charleston, Napa and Sonoma, Savannah, Cabo, St. Lucia, Maui and more, with fares for the Presidents' Day long weekend, Friday, February 12 to Monday, February 15.
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