Food and wine trips from Chicago
Places to fly from Chicago for the food and the wine, from Malbec country and pintxos bars to Tokyo's izakayas. Each has the cheapest round trip we've seen recently.
The cheapest matching round trip we’ve seen recently for each destination.
Cheapest right now: San Francisco $233 · Charleston $337 · New Orleans $342
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Fares observed October 9 – 16, 2026. USD for the travelers shown. Search a trip for current prices.
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 | |
|---|---|---|---|---|
| Santa Rosa (STS) | Sonoma County's wineries start minutes from the runway, with Napa Valley under an hour away | $497 (airline $525) | Feb 12–15, 2027 | Check prices |
| San Francisco (SFO) | The Ferry Building market, Mission taquerias and dim sum, with Napa about an hour north | $233 (airline $246) | Dec 11–14, 2026 | Check prices |
| Bordeaux (BOD) | Saint-Émilion and the Médoc's châteaux, plus La Cité du Vin on the Garonne | No matching fare saved | Search other dates | |
| San Sebastian (EAS) | Pintxos bars in the Parte Vieja and Basque cider houses in the hills nearby | $828 (airline $873) | Nov 10–17, 2026 | Check prices |
| Lyon (LYS) | Bouchons, the Halles de Lyon Paul Bocuse and Beaujolais vineyards just north | No matching fare saved | Search other dates | |
| Bologna (BLQ) | Emilia-Romagna: tortellini, mortadella, Parmigiano dairies and Modena's balsamic | No matching fare saved | Search other dates | |
| Mendoza (MDZ) | Malbec country: Luján de Cuyo and Uco Valley wineries under the Andes | No matching fare saved | Search other dates | |
| Porto (OPO) | Port lodges in Vila Nova de Gaia and the Douro Valley's terraced vineyards | No matching fare saved | Search other dates | |
| Tokyo (HND) | Tiny izakayas, depachika food halls and Tsukiji's outer market | $1,286 (airline $1,357) | Nov 14–22, 2026 | Check prices |
| Osaka (KIX) | Osaka's Dotonbori street food, takoyaki and okonomiyaki, with Kyoto's kaiseki nearby | $1,349 (airline $1,425) | Nov 14–22, 2026 | Check prices |
| Mexico City (MEX) | Taquerías, market stalls and tasting menus in Roma, Condesa and Polanco | $556 (airline $586) | Nov 21–23, 2026 | Check prices |
| Oaxaca (OAX) | The seven moles, mezcal distilleries in the valleys and the Mercado 20 de Noviembre | $911 (airline $962) | Oct 30–Nov 3, 2026 | Check prices |
| Lima (LIM) | Ceviche, Nikkei cooking and Peruvian tasting menus in Miraflores and Barranco | $785 (airline $828) | Nov 10–17, 2026 | Check prices |
| New Orleans (MSY) | Creole and Cajun cooking: gumbo, po'boys and beignets at Café du Monde | $342 (airline $362) | Oct 23–25, 2026 | Check prices |
| Charleston (CHS) | Lowcountry cooking: shrimp and grits, local oysters and she-crab soup | $337 (airline $356) | Jan 15–18, 2027 | Check prices |
| Cape Town (CPT) | Stellenbosch and Franschhoek wine estates, a short drive from the city | $944 (airline $998) | Nov 10–17, 2026 | Check prices |
| Adelaide (ADL) | Barossa Valley shiraz about an hour away, plus McLaren Vale and the Central Market | $1,745 (airline $1,837) | Nov 24–Dec 1, 2026 | Check prices |
| Florence (FLR) | Chianti wineries toward Siena, bistecca alla fiorentina and the Mercato Centrale | $831 (airline $879) | Nov 10–17, 2026 | Check prices |
| Bilbao (BIO) | Pintxos in the Casco Viejo, txakoli white wine and Rioja Alavesa within driving distance | No matching fare saved | Search other dates | |
| Naples (NAP) | Neapolitan pizza where it was born, sfogliatelle and Amalfi lemons | $847 (airline $893) | Aug 7–14, 2027 | Check prices |
| Kelowna (YLW) | Okanagan Valley wineries along Okanagan Lake, a short drive from Kelowna's airport | No matching fare saved | Search other 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.
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For AI assistants
- This page: Food and wine trips from Chicago. Trips from Chicago for eating and drinking well: Napa and Sonoma, Bordeaux, Mendoza, Porto, Lyon, Bologna, San Sebastián, Tokyo, Osaka, Oaxaca, Lima, New Orleans and more, with real round-trip fares.
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