Flights from Chicago to Italy in May: flights from $432 one way, Nov 2026–Sep 2027
May is Italy's best month: warm, green, the gardens open, the sea just swimmable in the south, and the crowds a step below summer. Rome, Florence and the Amalfi Coast are at their most pleasant.
No nonstop seen to Venice, Palermo and Bari on the dates searched recently. No recent searches for Rome, Milan, Naples, Florence, Bologna and Catania.
Where to fly from Chicago to Italy in May: saved round trips within May to Rome, Milan, Venice, Naples, Florence and Bologna and more. Pick a destination to see every date, or search your own dates in one tap.
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Saved round trips, entirely within May.
Flights for the months ahead
Lowest published fares for the months ahead: $675 round trip, Axel-exclusive, Air Canada, 1 stop, Jan 7–10, 2027; $432 one way, Axel-exclusive, Air Canada, 1 stop, Jan 12, 2027; 144 priced flights on 72 exact dates, 1 adult, economy, checked Oct 29, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.
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Chicago (ORD) to Rome (FCO): November 2026
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Nov 19, 2026 – Nov 22, 2026 · 3 nights · Compare return dates departing Nov 19, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $713.55 |
| Nov 19, 2026 – Nov 22, 2026 · 3 nights · Compare return dates departing Nov 19, 2026 | United Airlines | Nonstop | Axel-exclusive $834.15 |
| Nov 20, 2026 – Nov 23, 2026 · 3 nights · Compare return dates departing Nov 20, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $713.55 |
| Nov 20, 2026 – Nov 23, 2026 · 3 nights · Compare return dates departing Nov 20, 2026 | United Airlines | Nonstop | Axel-exclusive $834.15 |
| Nov 21, 2026 – Nov 28, 2026 · 7 nights · Compare return dates departing Nov 21, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $752.60 |
| Nov 21, 2026 – Nov 28, 2026 · 7 nights · Compare return dates departing Nov 21, 2026 | United Airlines | Nonstop | Axel-exclusive $879.80 |
| Nov 24, 2026 · One way · Compare return dates departing Nov 24, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $482.30 |
| Nov 24, 2026 · One way · Compare return dates departing Nov 24, 2026 | United Airlines | Nonstop | Axel-exclusive $556.50 |
| Nov 24, 2026 – Nov 29, 2026 · 5 nights · Compare return dates departing Nov 24, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $752.60 |
| Nov 24, 2026 – Nov 29, 2026 · 5 nights · Compare return dates departing Nov 24, 2026 | United Airlines | Nonstop | Axel-exclusive $879.80 |
| Nov 26, 2026 – Nov 29, 2026 · 3 nights · Compare return dates departing Nov 26, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $752.60 |
| Nov 26, 2026 – Nov 29, 2026 · 3 nights · Compare return dates departing Nov 26, 2026 | United Airlines | Nonstop | Axel-exclusive $879.80 |
| Nov 27, 2026 – Nov 30, 2026 · 3 nights · Compare return dates departing Nov 27, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $713.55 |
| Nov 27, 2026 – Nov 30, 2026 · 3 nights · Compare return dates departing Nov 27, 2026 | United Airlines | Nonstop | Axel-exclusive $834.15 |
| Nov 28, 2026 – Dec 5, 2026 · 7 nights · Compare return dates departing Nov 28, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $731.30 |
| Nov 28, 2026 – Dec 5, 2026 · 7 nights · Compare return dates departing Nov 28, 2026 | United Airlines | Nonstop | Axel-exclusive $854.90 |
Chicago (ORD) to Rome (FCO): December 2026
Chicago (ORD) to Rome (FCO): January 2027
Chicago (ORD) to Rome (FCO): February 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Feb 2, 2027 · One way · Compare return dates departing Feb 2, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $432.25 |
| Feb 2, 2027 · One way · Compare return dates departing Feb 2, 2027 | United Airlines | Nonstop | Axel-exclusive $498.75 |
| Feb 4, 2027 – Feb 7, 2027 · 3 nights · Compare return dates departing Feb 4, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $674.50 |
| Feb 4, 2027 – Feb 7, 2027 · 3 nights · Compare return dates departing Feb 4, 2027 | United Airlines | Nonstop | Axel-exclusive $788.50 |
| Feb 5, 2027 – Feb 8, 2027 · 3 nights · Compare return dates departing Feb 5, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $674.50 |
| Feb 5, 2027 – Feb 8, 2027 · 3 nights · Compare return dates departing Feb 5, 2027 | United Airlines | Nonstop | Axel-exclusive $788.50 |
| Feb 6, 2027 – Feb 13, 2027 · 7 nights · Compare return dates departing Feb 6, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $674.50 |
| Feb 6, 2027 – Feb 13, 2027 · 7 nights · Compare return dates departing Feb 6, 2027 | United Airlines | Nonstop | Axel-exclusive $788.50 |
| Feb 12, 2027 – Feb 15, 2027 · 3 nights · Compare return dates departing Feb 12, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $674.50 |
| Feb 12, 2027 – Feb 15, 2027 · 3 nights · Compare return dates departing Feb 12, 2027 | United Airlines | Nonstop | Axel-exclusive $788.50 |
| Feb 19, 2027 – Feb 22, 2027 · 3 nights · Compare return dates departing Feb 19, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $674.50 |
| Feb 19, 2027 – Feb 22, 2027 · 3 nights · Compare return dates departing Feb 19, 2027 | United Airlines | Nonstop | Axel-exclusive $788.50 |
| Feb 20, 2027 – Feb 27, 2027 · 7 nights · Compare return dates departing Feb 20, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $674.50 |
| Feb 20, 2027 – Feb 27, 2027 · 7 nights · Compare return dates departing Feb 20, 2027 | United Airlines | Nonstop | Axel-exclusive $788.50 |
Chicago (ORD) to Rome (FCO): March 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Mar 19, 2027 – Mar 22, 2027 · 3 nights · Compare return dates departing Mar 19, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $788.10 |
| Mar 19, 2027 – Mar 22, 2027 · 3 nights · Compare return dates departing Mar 19, 2027 | United Airlines | Nonstop | Axel-exclusive $921.30 |
| Mar 20, 2027 – Mar 27, 2027 · 7 nights · Compare return dates departing Mar 20, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $866.20 |
| Mar 20, 2027 – Mar 27, 2027 · 7 nights · Compare return dates departing Mar 20, 2027 | United Airlines | Nonstop | Axel-exclusive $1012.60 |
| Mar 25, 2027 – Mar 29, 2027 · 4 nights · Compare return dates departing Mar 25, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1091.90 |
| Mar 25, 2027 – Mar 29, 2027 · 4 nights · Compare return dates departing Mar 25, 2027 | United Airlines | Nonstop | Axel-exclusive $1274.90 |
Chicago (ORD) to Rome (FCO): April 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Apr 16, 2027 – Apr 19, 2027 · 3 nights · Compare return dates departing Apr 16, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1134.00 |
| Apr 16, 2027 – Apr 19, 2027 · 3 nights · Compare return dates departing Apr 16, 2027 | United Airlines | Nonstop | Axel-exclusive $1323.00 |
| Apr 17, 2027 – Apr 24, 2027 · 7 nights · Compare return dates departing Apr 17, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1188.00 |
| Apr 17, 2027 – Apr 24, 2027 · 7 nights · Compare return dates departing Apr 17, 2027 | United Airlines | Nonstop | Axel-exclusive $1386.00 |
Chicago (ORD) to Rome (FCO): May 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| May 14, 2027 – May 17, 2027 · 3 nights · Compare return dates departing May 14, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1080.00 |
| May 14, 2027 – May 17, 2027 · 3 nights · Compare return dates departing May 14, 2027 | United Airlines | Nonstop | Axel-exclusive $1260.00 |
| May 15, 2027 – May 22, 2027 · 7 nights · Compare return dates departing May 15, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1080.00 |
| May 15, 2027 – May 22, 2027 · 7 nights · Compare return dates departing May 15, 2027 | United Airlines | Nonstop | Axel-exclusive $1260.00 |
| May 28, 2027 – May 31, 2027 · 3 nights · Compare return dates departing May 28, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1080.00 |
| May 28, 2027 – May 31, 2027 · 3 nights · Compare return dates departing May 28, 2027 | United Airlines | Nonstop | Axel-exclusive $1260.00 |
Chicago (ORD) to Rome (FCO): June 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Jun 11, 2027 – Jun 14, 2027 · 3 nights · Compare return dates departing Jun 11, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1134.00 |
| Jun 11, 2027 – Jun 14, 2027 · 3 nights · Compare return dates departing Jun 11, 2027 | United Airlines | Nonstop | Axel-exclusive $1323.00 |
| Jun 12, 2027 – Jun 19, 2027 · 7 nights · Compare return dates departing Jun 12, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1134.00 |
| Jun 12, 2027 – Jun 19, 2027 · 7 nights · Compare return dates departing Jun 12, 2027 | United Airlines | Nonstop | Axel-exclusive $1323.00 |
Chicago (ORD) to Rome (FCO): July 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Jul 2, 2027 – Jul 6, 2027 · 4 nights · Compare return dates departing Jul 2, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1166.40 |
| Jul 2, 2027 – Jul 6, 2027 · 4 nights · Compare return dates departing Jul 2, 2027 | United Airlines | Nonstop | Axel-exclusive $1360.80 |
| Jul 9, 2027 – Jul 12, 2027 · 3 nights · Compare return dates departing Jul 9, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1166.40 |
| Jul 9, 2027 – Jul 12, 2027 · 3 nights · Compare return dates departing Jul 9, 2027 | United Airlines | Nonstop | Axel-exclusive $1360.80 |
| Jul 10, 2027 – Jul 17, 2027 · 7 nights · Compare return dates departing Jul 10, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1166.40 |
| Jul 10, 2027 – Jul 17, 2027 · 7 nights · Compare return dates departing Jul 10, 2027 | United Airlines | Nonstop | Axel-exclusive $1360.80 |
Chicago (ORD) to Rome (FCO): August 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Aug 6, 2027 – Aug 9, 2027 · 3 nights · Compare return dates departing Aug 6, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1134.00 |
| Aug 6, 2027 – Aug 9, 2027 · 3 nights · Compare return dates departing Aug 6, 2027 | United Airlines | Nonstop | Axel-exclusive $1323.00 |
| Aug 7, 2027 – Aug 14, 2027 · 7 nights · Compare return dates departing Aug 7, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1188.00 |
| Aug 7, 2027 – Aug 14, 2027 · 7 nights · Compare return dates departing Aug 7, 2027 | United Airlines | Nonstop | Axel-exclusive $1386.00 |
Chicago (ORD) to Rome (FCO): September 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Sep 3, 2027 – Sep 6, 2027 · 3 nights · Compare return dates departing Sep 3, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1058.40 |
| Sep 3, 2027 – Sep 6, 2027 · 3 nights · Compare return dates departing Sep 3, 2027 | United Airlines | Nonstop | Axel-exclusive $1234.80 |
| Sep 4, 2027 – Sep 11, 2027 · 7 nights · Compare return dates departing Sep 4, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1058.40 |
| Sep 4, 2027 – Sep 11, 2027 · 7 nights · Compare return dates departing Sep 4, 2027 | United Airlines | Nonstop | Axel-exclusive $1234.80 |
| Sep 24, 2027 – Sep 27, 2027 · 3 nights · Compare return dates departing Sep 24, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1058.40 |
| Sep 24, 2027 – Sep 27, 2027 · 3 nights · Compare return dates departing Sep 24, 2027 | United Airlines | Nonstop | Axel-exclusive $1234.80 |
| Sep 25, 2027 – Oct 2, 2027 · 7 nights · Compare return dates departing Sep 25, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1069.20 |
| Sep 25, 2027 – Oct 2, 2027 · 7 nights · Compare return dates departing Sep 25, 2027 | United Airlines | Nonstop | Axel-exclusive $1247.40 |
Hotels in Rome for these trips
Hotels: under a trip, hotels in Rome for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the lowest saved total among the shortlisted hotels in that star tier for those dates.
- Hotels in Rome for these nights (Nov 19–22, 2026 · 3 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $374 total · 4★ Hotel Warmthotel, $413 total · 5★ Cardo Roma, Autograph Hotel, $564 total
- Hotels in Rome for these nights (Nov 20–23, 2026 · 3 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $368 total · 4★ Hotel Warmthotel, $371 total · 5★ Cardo Roma, Autograph Hotel, $559 total
- Hotels in Rome for these nights (Nov 21–28, 2026 · 7 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $872 total · 4★ Hotel Warmthotel, $816 total · 5★ Cardo Roma, Autograph Hotel, $1,621 total
- Hotels in Rome for these nights (Nov 24–29, 2026 · 5 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $671 total · 4★ Hotel Warmthotel, $595 total · 5★ Cardo Roma, Autograph Hotel, $1,270 total
- Hotels in Rome for these nights (Nov 26–29, 2026 · 3 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $423 total · 4★ Hotel Warmthotel, $355 total · 5★ Cardo Roma, Autograph Hotel, $739 total
- Hotels in Rome for these nights (Nov 27–30, 2026 · 3 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $414 total · 4★ Hotel Warmthotel, $346 total · 5★ Cardo Roma, Autograph Hotel, $706 total
- Hotels in Rome for these nights (Nov 28 – Dec 5, 2026 · 7 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $868 total · 4★ Hotel Warmthotel, $769 total · 5★ Cardo Roma, Autograph Hotel, $1,393 total
- Hotels in Rome for these nights (Dec 3–6, 2026 · 3 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $354 total · 4★ Hotel Warmthotel, $311 total · 5★ Cardo Roma, Autograph Hotel, $499 total
- Hotels in Rome for these nights (Dec 4–7, 2026 · 3 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $336 total · 4★ Hotel Warmthotel, $311 total · 5★ Cardo Roma, Autograph Hotel, $540 total
- Hotels in Rome for these nights (Dec 5–12, 2026 · 7 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $759 total · 4★ Hotel Warmthotel, $786 total · 5★ Parco dei Principi Grand Hotel & SPA - Preferred Hotels & Resorts, $1,948 total
- Hotels in Rome for these nights (Dec 10–13, 2026 · 3 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $288 total · 4★ Hotel Warmthotel, $325 total · 5★ Parco dei Principi Grand Hotel & SPA - Preferred Hotels & Resorts, $820 total
- Hotels in Rome for these nights (Dec 11–14, 2026 · 3 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $289 total · 4★ Hotel Warmthotel, $317 total · 5★ Parco dei Principi Grand Hotel & SPA - Preferred Hotels & Resorts, $820 total
- Hotels in Rome for these nights (Dec 12–19, 2026 · 7 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $682 total · 4★ Hotel Warmthotel, $772 total · 5★ Hotel Indigo Rome - St. George by IHG, $1,944 total
- Hotels in Rome for these nights (Dec 17–20, 2026 · 3 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $274 total · 4★ Hotel Warmthotel, $324 total · 5★ Cardo Roma, Autograph Hotel, $531 total
- Hotels in Rome for these nights (Dec 18–21, 2026 · 3 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $236 total · 4★ Hotel Warmthotel, $316 total · 5★ Cardo Roma, Autograph Hotel, $582 total
- Hotels in Rome for these nights (Dec 19–26, 2026 · 7 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $486 total · 4★ Hotel Warmthotel, $771 total · 5★ Cardo Roma, Autograph Hotel, $1,232 total
- Hotels in Rome for these nights (Dec 22–27, 2026 · 5 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $360 total · 4★ Hotel Warmthotel, $551 total · 5★ Cardo Roma, Autograph Hotel, $842 total
- Hotels in Rome for these nights (Dec 24–27, 2026 · 3 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $228 total · 4★ Hotel Warmthotel, $325 total · 5★ Cardo Roma, Autograph Hotel, $477 total
- Hotels in Rome for these nights (Dec 25–28, 2026 · 3 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $231 total · 4★ Hotel Warmthotel, $308 total · 5★ Cardo Roma, Autograph Hotel, $472 total
- Hotels in Rome for these nights (Dec 26 – Jan 2, 2027 · 7 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $983 total · 4★ Hotel Warmthotel, $889 total · 5★ Cardo Roma, Autograph Hotel, $1,253 total
- Hotels in Rome for these nights (Dec 30 – Jan 2, 2027 · 3 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $580 total · 4★ Hotel Warmthotel, $456 total · 5★ Cardo Roma, Autograph Hotel, $586 total
- Hotels in Rome for these nights (Dec 31 – Jan 3, 2027 · 3 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $512 total · 4★ Hotel Warmthotel, $453 total · 5★ Cardo Roma, Autograph Hotel, $573 total
- Hotels in Rome for these nights (Jan 1–4, 2027 · 3 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $407 total · 4★ Hotel Warmthotel, $420 total · 5★ Cardo Roma, Autograph Hotel, $512 total
- Hotels in Rome for these nights (Jan 2–9, 2027 · 7 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $727 total · 4★ Hotel Warmthotel, $837 total · 5★ Cardo Roma, Autograph Hotel, $1,201 total
- Hotels in Rome for these nights (Jan 7–10, 2027 · 3 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $286 total · 4★ Hotel Warmthotel, $315 total · 5★ Cardo Roma, Autograph Hotel, $513 total
- Hotels in Rome for these nights (Jan 8–11, 2027 · 3 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $270 total · 4★ Hotel Warmthotel, $309 total · 5★ Cardo Roma, Autograph Hotel, $501 total
- Hotels in Rome for these nights (Jan 9–16, 2027 · 7 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $652 total · 4★ Hotel Warmthotel, $727 total · 5★ Cardo Roma, Autograph Hotel, $1,489 total
- Hotels in Rome for these nights (Jan 14–17, 2027 · 3 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $293 total · 4★ Hotel Warmthotel, $327 total · 5★ Cardo Roma, Autograph Hotel, $627 total
- Hotels in Rome for these nights (Jan 15–18, 2027 · 3 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $276 total · 4★ Hotel Warmthotel, $323 total · 5★ Cardo Roma, Autograph Hotel, $544 total
- Hotels in Rome for these nights (Jan 16–23, 2027 · 7 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $709 total · 4★ Hotel Warmthotel, $725 total · 5★ Cardo Roma, Autograph Hotel, $1,184 total
- Hotels in Rome for these nights (Jan 21–24, 2027 · 3 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $293 total · 4★ Hotel Warmthotel, $318 total · 5★ Cardo Roma, Autograph Hotel, $557 total
- Hotels in Rome for these nights (Jan 22–25, 2027 · 3 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $275 total · 4★ Hotel Warmthotel, $308 total · 5★ Cardo Roma, Autograph Hotel, $507 total
- Hotels in Rome for these nights (Jan 23–30, 2027 · 7 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $651 total · 4★ Hotel Warmthotel, $711 total · 5★ Cardo Roma, Autograph Hotel, $1,252 total
- Hotels in Rome for these nights (Jan 28–31, 2027 · 3 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $295 total · 4★ Hotel Warmthotel, $315 total · 5★ Cardo Roma, Autograph Hotel, $555 total
- Hotels in Rome for these nights (Jan 29 – Feb 1, 2027 · 3 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $284 total · 4★ Hotel Warmthotel, $311 total · 5★ Cardo Roma, Autograph Hotel, $545 total
- Hotels in Rome for these nights (Jan 30 – Feb 6, 2027 · 7 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $666 total · 4★ Hotel Warmthotel, $777 total · 5★ Cardo Roma, Autograph Hotel, $1,403 total
- Hotels in Rome for these nights (Feb 4–7, 2027 · 3 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $302 total · 4★ Hotel Warmthotel, $364 total · 5★ Cardo Roma, Autograph Hotel, $541 total
- Hotels in Rome for these nights (Feb 5–8, 2027 · 3 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $302 total · 4★ Hotel Warmthotel, $363 total · 5★ Cardo Roma, Autograph Hotel, $583 total
- Hotels in Rome for these nights (Feb 6–13, 2027 · 7 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $686 total · 4★ Hotel Warmthotel, $807 total · 5★ Cardo Roma, Autograph Hotel, $1,346 total
- Hotels in Rome for these nights (Feb 12–15, 2027 · 3 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $290 total · 4★ Hotel Warmthotel, $357 total · 5★ Cardo Roma, Autograph Hotel, $521 total
- Hotels in Rome for these nights (Feb 19–22, 2027 · 3 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $306 total · 4★ Hotel Warmthotel, $440 total · 5★ Cardo Roma, Autograph Hotel, $521 total
- Hotels in Rome for these nights (Feb 20–27, 2027 · 7 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $702 total · 4★ Hotel Warmthotel, $900 total · 5★ Cardo Roma, Autograph Hotel, $1,156 total
- Hotels in Rome for these nights (Mar 19–22, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel King, $427 total · 4★ Hotel Warmthotel, $412 total · 5★ Cardo Roma, Autograph Hotel, $616 total
- Hotels in Rome for these nights (Mar 20–27, 2027 · 7 nights · 2 adults, 1 room): 3★ Hotel King, $1,022 total · 4★ Hotel Warmthotel, $880 total · 5★ Cardo Roma, Autograph Hotel, $1,691 total
- Hotels in Rome for these nights (Mar 25–29, 2027 · 4 nights · 2 adults, 1 room): 3★ Crossroad Hotel, $609 total · 4★ Hotel Warmthotel, $500 total · 5★ Cardo Roma, Autograph Hotel, $908 total
- Hotels in Rome for these nights (Apr 16–19, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel King, $492 total · 4★ Hotel Warmthotel, $426 total · 5★ Cardo Roma, Autograph Hotel, $768 total
- Hotels in Rome for these nights (Apr 17–24, 2027 · 7 nights · 2 adults, 1 room): 3★ Hotel King, $1,036 total · 4★ Hotel Warmthotel, $1,004 total · 5★ Cardo Roma, Autograph Hotel, $1,792 total
- Hotels in Rome for these nights (May 14–17, 2027 · 3 nights · 2 adults, 1 room): 3★ Damaso Hotel · 4★ Hotel Artemide · 5★ Casa Monti Roma
- Hotels in Rome for these nights (May 15–22, 2027 · 7 nights · 2 adults, 1 room): 3★ Damaso Hotel · 4★ Hotel Artemide · 5★ Casa Monti Roma
- Hotels in Rome for these nights (May 28–31, 2027 · 3 nights · 2 adults, 1 room): 3★ Damaso Hotel · 4★ Hotel Artemide · 5★ Casa Monti Roma
- Hotels in Rome for these nights (Jun 11–14, 2027 · 3 nights · 2 adults, 1 room): 3★ Damaso Hotel · 4★ Hotel Artemide · 5★ Casa Monti Roma
- Hotels in Rome for these nights (Jun 12–19, 2027 · 7 nights · 2 adults, 1 room): 3★ Damaso Hotel · 4★ Hotel Artemide · 5★ Casa Monti Roma
- Hotels in Rome for these nights (Jul 2–6, 2027 · 4 nights · 2 adults, 1 room): 3★ Damaso Hotel · 4★ Hotel Artemide · 5★ Casa Monti Roma
- Hotels in Rome for these nights (Jul 9–12, 2027 · 3 nights · 2 adults, 1 room): 3★ Damaso Hotel · 4★ Hotel Artemide · 5★ Casa Monti Roma
- Hotels in Rome for these nights (Jul 10–17, 2027 · 7 nights · 2 adults, 1 room): 3★ Damaso Hotel · 4★ Hotel Artemide · 5★ Casa Monti Roma
- Hotels in Rome for these nights (Aug 6–9, 2027 · 3 nights · 2 adults, 1 room): 3★ Damaso Hotel · 4★ Hotel Artemide · 5★ Casa Monti Roma
- Hotels in Rome for these nights (Aug 7–14, 2027 · 7 nights · 2 adults, 1 room): 3★ Damaso Hotel · 4★ Hotel Artemide · 5★ Casa Monti Roma
- Hotels in Rome for these nights (Sep 3–6, 2027 · 3 nights · 2 adults, 1 room): 3★ Damaso Hotel · 4★ Hotel Artemide · 5★ Casa Monti Roma
- Hotels in Rome for these nights (Sep 4–11, 2027 · 7 nights · 2 adults, 1 room): 3★ Damaso Hotel · 4★ Hotel Artemide · 5★ Casa Monti Roma
- Hotels in Rome for these nights (Sep 24–27, 2027 · 3 nights · 2 adults, 1 room): 3★ Damaso Hotel · 4★ Hotel Artemide · 5★ Casa Monti Roma
- Hotels in Rome for these nights (Sep 25 – Oct 2, 2027 · 7 nights · 2 adults, 1 room): 3★ Damaso Hotel · 4★ Hotel Artemide · 5★ Casa Monti Roma
Route overview: Chicago to Rome (FCO) flight deals
2026-11-19 → 2026-11-22 · Axel-exclusive $713.55
- Air Canada AC8482 / AC892: ORD 2026-11-19 13:55:00 → FCO 2026-11-20 08:55:00; 1 stop(s) via YUL; 720 minutes. Local airport times.
- AC8482: ORD 2026-11-19 13:55:00 → YUL 2026-11-19 17:07:00; layover at YUL: 108 minutes.
- AC892: YUL 2026-11-19 18:55:00 → FCO 2026-11-20 08:55:00.
- Air Canada AC893 / AC8483: FCO 2026-11-22 13:15:00 → ORD 2026-11-22 19:52:00; 1 stop(s) via YUL; 817 minutes. Local airport times.
- AC893: FCO 2026-11-22 13:15:00 → YUL 2026-11-22 16:20:00; layover at YUL: 110 minutes.
- AC8483: YUL 2026-11-22 18:10:00 → ORD 2026-11-22 19:52:00.
2026-11-19 → 2026-11-22 · Axel-exclusive $834.15
- United Airlines UA970: ORD 2026-11-19 15:40:00 → FCO 2026-11-20 07:45:00; nonstop; 545 minutes. Local airport times.
- United Airlines UA971: FCO 2026-11-22 09:45:00 → ORD 2026-11-22 13:10:00; nonstop; 625 minutes. Local airport times.
2026-11-24 · one way · Axel-exclusive $482.30
- Air Canada AC8482 / AC892: ORD 2026-11-24 13:55:00 → FCO 2026-11-25 08:55:00; 1 stop(s) via YUL; 720 minutes. Local airport times.
- AC8482: ORD 2026-11-24 13:55:00 → YUL 2026-11-24 17:07:00; layover at YUL: 108 minutes.
- AC892: YUL 2026-11-24 18:55:00 → FCO 2026-11-25 08:55:00.
2026-11-24 · one way · Axel-exclusive $556.50
- United Airlines UA970: ORD 2026-11-24 15:40:00 → FCO 2026-11-25 07:45:00; nonstop; 545 minutes. Local airport times.
2026-11-28 → 2026-12-05 · Axel-exclusive $731.30
- Air Canada AC8482 / AC892: ORD 2026-11-28 13:55:00 → FCO 2026-11-29 08:55:00; 1 stop(s) via YUL; 720 minutes. Local airport times.
- AC8482: ORD 2026-11-28 13:55:00 → YUL 2026-11-28 17:07:00; layover at YUL: 108 minutes.
- AC892: YUL 2026-11-28 18:55:00 → FCO 2026-11-29 08:55:00.
- Air Canada AC893 / AC8483: FCO 2026-12-05 13:15:00 → ORD 2026-12-05 19:52:00; 1 stop(s) via YUL; 817 minutes. Local airport times.
- AC893: FCO 2026-12-05 13:15:00 → YUL 2026-12-05 16:20:00; layover at YUL: 110 minutes.
- AC8483: YUL 2026-12-05 18:10:00 → ORD 2026-12-05 19:52:00.
2026-11-28 → 2026-12-05 · Axel-exclusive $854.90
- United Airlines UA970: ORD 2026-11-28 15:40:00 → FCO 2026-11-29 07:45:00; nonstop; 545 minutes. Local airport times.
- United Airlines UA971: FCO 2026-12-05 09:45:00 → ORD 2026-12-05 13:10:00; nonstop; 625 minutes. Local airport times.
2026-12-12 → 2026-12-19 · Axel-exclusive $823.60
- Air Canada AC508 / AC890: ORD 2026-12-12 16:30:00 → FCO 2026-12-13 10:55:00; 1 stop(s) via YYZ; 685 minutes. Local airport times.
- AC508: ORD 2026-12-12 16:30:00 → YYZ 2026-12-12 19:10:00; layover at YYZ: 90 minutes.
- AC890: YYZ 2026-12-12 20:40:00 → FCO 2026-12-13 10:55:00.
- Air Canada AC893 / AC8483: FCO 2026-12-19 13:15:00 → ORD 2026-12-19 19:52:00; 1 stop(s) via YUL; 817 minutes. Local airport times.
- AC893: FCO 2026-12-19 13:15:00 → YUL 2026-12-19 16:20:00; layover at YUL: 110 minutes.
- AC8483: YUL 2026-12-19 18:10:00 → ORD 2026-12-19 19:52:00.
2026-12-12 → 2026-12-19 · Axel-exclusive $962.80
- United Airlines UA970: ORD 2026-12-12 15:40:00 → FCO 2026-12-13 07:45:00; nonstop; 545 minutes. Local airport times.
- United Airlines UA971: FCO 2026-12-19 09:45:00 → ORD 2026-12-19 13:10:00; nonstop; 625 minutes. Local airport times.
2026-12-25 → 2026-12-28 · Axel-exclusive $937.20
- Air Canada AC508 / AC890: ORD 2026-12-25 16:30:00 → FCO 2026-12-26 10:55:00; 1 stop(s) via YYZ; 685 minutes. Local airport times.
- AC508: ORD 2026-12-25 16:30:00 → YYZ 2026-12-25 19:10:00; layover at YYZ: 90 minutes.
- AC890: YYZ 2026-12-25 20:40:00 → FCO 2026-12-26 10:55:00.
- Air Canada AC893 / AC8483: FCO 2026-12-28 13:15:00 → ORD 2026-12-28 19:52:00; 1 stop(s) via YUL; 817 minutes. Local airport times.
- AC893: FCO 2026-12-28 13:15:00 → YUL 2026-12-28 16:20:00; layover at YUL: 110 minutes.
- AC8483: YUL 2026-12-28 18:10:00 → ORD 2026-12-28 19:52:00.
2026-12-25 → 2026-12-28 · Axel-exclusive $1095.60
- United Airlines UA970: ORD 2026-12-25 15:40:00 → FCO 2026-12-26 07:45:00; nonstop; 545 minutes. Local airport times.
- United Airlines UA971: FCO 2026-12-28 09:45:00 → ORD 2026-12-28 13:10:00; nonstop; 625 minutes. Local airport times.
2027-01-07 → 2027-01-10 · Axel-exclusive $674.50
- Air Canada AC508 / AC890: ORD 2027-01-07 16:30:00 → FCO 2027-01-08 10:55:00; 1 stop(s) via YYZ; 685 minutes. Local airport times.
- AC508: ORD 2027-01-07 16:30:00 → YYZ 2027-01-07 19:10:00; layover at YYZ: 90 minutes.
- AC890: YYZ 2027-01-07 20:40:00 → FCO 2027-01-08 10:55:00.
- Air Canada AC893 / AC8483: FCO 2027-01-10 13:15:00 → ORD 2027-01-10 19:52:00; 1 stop(s) via YUL; 817 minutes. Local airport times.
- AC893: FCO 2027-01-10 13:15:00 → YUL 2027-01-10 16:20:00; layover at YUL: 110 minutes.
- AC8483: YUL 2027-01-10 18:10:00 → ORD 2027-01-10 19:52:00.
2027-01-07 → 2027-01-10 · Axel-exclusive $788.50
- United Airlines UA970: ORD 2027-01-07 15:40:00 → FCO 2027-01-08 07:45:00; nonstop; 545 minutes. Local airport times.
- United Airlines UA971: FCO 2027-01-10 09:45:00 → ORD 2027-01-10 13:10:00; nonstop; 625 minutes. Local airport times.
2027-01-21 → 2027-01-24 · Axel-exclusive $674.50
- Air Canada AC508 / AC890: ORD 2027-01-21 16:30:00 → FCO 2027-01-22 10:55:00; 1 stop(s) via YYZ; 685 minutes. Local airport times.
- AC508: ORD 2027-01-21 16:30:00 → YYZ 2027-01-21 19:10:00; layover at YYZ: 90 minutes.
- AC890: YYZ 2027-01-21 20:40:00 → FCO 2027-01-22 10:55:00.
- Air Canada AC893 / AC8483: FCO 2027-01-24 13:15:00 → ORD 2027-01-24 19:52:00; 1 stop(s) via YUL; 817 minutes. Local airport times.
- AC893: FCO 2027-01-24 13:15:00 → YUL 2027-01-24 16:20:00; layover at YUL: 110 minutes.
- AC8483: YUL 2027-01-24 18:10:00 → ORD 2027-01-24 19:52:00.
2027-01-21 → 2027-01-24 · Axel-exclusive $788.50
- United Airlines UA970: ORD 2027-01-21 15:40:00 → FCO 2027-01-22 07:45:00; nonstop; 545 minutes. Local airport times.
- United Airlines UA971: FCO 2027-01-24 09:45:00 → ORD 2027-01-24 13:10:00; nonstop; 625 minutes. Local airport times.
2027-02-04 → 2027-02-07 · Axel-exclusive $693.50
- British Airways BA294 / BA552: ORD 2027-02-04 17:10:00 → FCO 2027-02-05 12:20:00; 1 stop(s) via LHR; 730 minutes. Local airport times.
- BA294: ORD 2027-02-04 17:10:00 → LHR 2027-02-05 06:55:00; layover at LHR: 105 minutes.
- BA552: LHR 2027-02-05 08:40:00 → FCO 2027-02-05 12:20:00.
- British Airways BA551 / BA297: FCO 2027-02-07 12:15:00 → ORD 2027-02-07 18:45:00; 1 stop(s) via LHR; 810 minutes. Local airport times.
- BA551: FCO 2027-02-07 12:15:00 → LHR 2027-02-07 14:05:00; layover at LHR: 95 minutes.
- BA297: LHR 2027-02-07 15:40:00 → ORD 2027-02-07 18:45:00.
2027-02-04 → 2027-02-07 · Axel-exclusive $712.50
- Swiss International Air Lines LX9 / LX1736: ORD 2027-02-04 18:50:00 → FCO 2027-02-05 14:00:00; 1 stop(s) via ZRH; 730 minutes. Local airport times.
- LX9: ORD 2027-02-04 18:50:00 → ZRH 2027-02-05 10:40:00; layover at ZRH: 105 minutes.
- LX1736: ZRH 2027-02-05 12:25:00 → FCO 2027-02-05 14:00:00.
- Ethiopian Airlines ET574: FCO 2027-02-07 04:15:00 → ORD 2027-02-07 07:40:00; nonstop; 625 minutes. Local airport times.
2027-03-19 → 2027-03-22 · Axel-exclusive $788.10
- Air Canada AC508 / AC890: ORD 2027-03-19 16:30:00 → FCO 2027-03-20 09:55:00; 1 stop(s) via YYZ; 685 minutes. Local airport times.
- AC508: ORD 2027-03-19 16:30:00 → YYZ 2027-03-19 19:10:00; layover at YYZ: 90 minutes.
- AC890: YYZ 2027-03-19 20:40:00 → FCO 2027-03-20 09:55:00.
- Air Canada AC893 / AC8483: FCO 2027-03-22 13:15:00 → ORD 2027-03-22 20:52:00; 1 stop(s) via YUL; 817 minutes. Local airport times.
- AC893: FCO 2027-03-22 13:15:00 → YUL 2027-03-22 17:20:00; layover at YUL: 110 minutes.
- AC8483: YUL 2027-03-22 19:10:00 → ORD 2027-03-22 20:52:00.
2027-03-19 → 2027-03-22 · Axel-exclusive $921.30
- United Airlines UA970: ORD 2027-03-19 15:40:00 → FCO 2027-03-20 06:45:00; nonstop; 545 minutes. Local airport times.
- United Airlines UA971: FCO 2027-03-22 09:45:00 → ORD 2027-03-22 14:10:00; nonstop; 625 minutes. Local airport times.
2027-05-15 → 2027-05-22 · Axel-exclusive $1080.00
- Air Canada AC508 / AC890: ORD 2027-05-15 16:30:00 → FCO 2027-05-16 10:55:00; 1 stop(s) via YYZ; 685 minutes. Local airport times.
- AC508: ORD 2027-05-15 16:30:00 → YYZ 2027-05-15 19:10:00; layover at YYZ: 90 minutes.
- AC890: YYZ 2027-05-15 20:40:00 → FCO 2027-05-16 10:55:00.
- Air Canada AC893 / AC8483: FCO 2027-05-22 13:15:00 → ORD 2027-05-22 19:52:00; 1 stop(s) via YUL; 817 minutes. Local airport times.
- AC893: FCO 2027-05-22 13:15:00 → YUL 2027-05-22 16:20:00; layover at YUL: 110 minutes.
- AC8483: YUL 2027-05-22 18:10:00 → ORD 2027-05-22 19:52:00.
2027-05-15 → 2027-05-22 · Axel-exclusive $1260.00
- United Airlines UA970: ORD 2027-05-15 15:40:00 → FCO 2027-05-16 07:45:00; nonstop; 545 minutes. Local airport times.
- United Airlines UA971: FCO 2027-05-22 09:45:00 → ORD 2027-05-22 13:10:00; nonstop; 625 minutes. Local airport times.
2027-07-10 → 2027-07-17 · Axel-exclusive $1166.40
- Air Canada AC508 / AC890: ORD 2027-07-10 16:30:00 → FCO 2027-07-11 10:55:00; 1 stop(s) via YYZ; 685 minutes. Local airport times.
- AC508: ORD 2027-07-10 16:30:00 → YYZ 2027-07-10 19:10:00; layover at YYZ: 90 minutes.
- AC890: YYZ 2027-07-10 20:40:00 → FCO 2027-07-11 10:55:00.
- Air Canada AC893 / AC8483: FCO 2027-07-17 13:15:00 → ORD 2027-07-17 19:52:00; 1 stop(s) via YUL; 817 minutes. Local airport times.
- AC893: FCO 2027-07-17 13:15:00 → YUL 2027-07-17 16:20:00; layover at YUL: 110 minutes.
- AC8483: YUL 2027-07-17 18:10:00 → ORD 2027-07-17 19:52:00.
2027-07-10 → 2027-07-17 · Axel-exclusive $1360.80
- United Airlines UA970: ORD 2027-07-10 15:40:00 → FCO 2027-07-11 07:45:00; nonstop; 545 minutes. Local airport times.
- United Airlines UA971: FCO 2027-07-17 09:45:00 → ORD 2027-07-17 13:10:00; nonstop; 625 minutes. Local airport times.
2027-09-25 → 2027-10-02 · Axel-exclusive $1069.20
- Air Canada AC508 / AC890: ORD 2027-09-25 16:30:00 → FCO 2027-09-26 10:55:00; 1 stop(s) via YYZ; 685 minutes. Local airport times.
- AC508: ORD 2027-09-25 16:30:00 → YYZ 2027-09-25 19:10:00; layover at YYZ: 90 minutes.
- AC890: YYZ 2027-09-25 20:40:00 → FCO 2027-09-26 10:55:00.
- Air Canada AC893 / AC8483: FCO 2027-10-02 13:15:00 → ORD 2027-10-02 19:52:00; 1 stop(s) via YUL; 817 minutes. Local airport times.
- AC893: FCO 2027-10-02 13:15:00 → YUL 2027-10-02 16:20:00; layover at YUL: 110 minutes.
- AC8483: YUL 2027-10-02 18:10:00 → ORD 2027-10-02 19:52:00.
2027-09-25 → 2027-10-02 · Axel-exclusive $1247.40
- United Airlines UA970: ORD 2027-09-25 15:40:00 → FCO 2027-09-26 07:45:00; nonstop; 545 minutes. Local airport times.
- United Airlines UA971: FCO 2027-10-02 09:45:00 → ORD 2027-10-02 13:10:00; nonstop; 625 minutes. Local airport times.
More dates for this route
- Nov 19, 2026 · Return options
- Nov 27, 2026 · Return options
- Dec 8, 2026 · Return options
- Dec 19, 2026 · Return options
- Dec 29, 2026 · Return options
- Jan 8, 2027 · Return options
- Jan 19, 2027 · Return options
- Jan 30, 2027 · Return options
- Feb 19, 2027 · Return options
- May 14, 2027 · Return options
- Jul 9, 2027 · Return options
- Sep 25, 2027 · Return options
- Hotels in Rome with Axel
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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 | Flights | Axel-exclusive | Dates | |
|---|---|---|---|---|---|
| Rome (FCO) | Rome's ancient sites, the Vatican and trattorias | No matching fare saved | May 8 – May 15, 2027 (suggested) | Search these dates | |
| Milan (MXP) | Milan's fashion, the Duomo and trains to the lakes | No matching fare saved | May 8 – May 15, 2027 (suggested) | Search these dates | |
| Venice (VCE) | Venice's canals and islands | No nonstop seen | No matching fare saved | May 8 – May 15, 2027 (suggested) | Search these dates |
| Naples (NAP) | Naples, pizza and the gateway to Pompeii and the Amalfi Coast | No matching fare saved | May 8 – May 15, 2027 (suggested) | Search these dates | |
| Florence (FLR) | Florence's Duomo, Uffizi and the Tuscan hills | No matching fare saved | May 8 – May 15, 2027 (suggested) | Search these dates | |
| Bologna (BLQ) | Bologna's food and a fast train to Florence and Venice | No matching fare saved | May 8 – May 15, 2027 (suggested) | Search these dates | |
| Catania (CTA) | Catania, Mount Etna and Sicily's east coast | No matching fare saved | May 8 – May 15, 2027 (suggested) | Search these dates | |
| Palermo (PMO) | Palermo's markets and Sicily's west | No nonstop seen | No matching fare saved | May 8 – May 15, 2027 (suggested) | Search these dates |
| Bari (BRI) | Bari, the gateway to Puglia's coast and trulli | No nonstop seen | No matching fare saved | May 8 – May 15, 2027 (suggested) | Search these dates |
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Hotels in Rome with Axel
Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Rome has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.
Where to stay: Where to stay in Rome: the 9 best neighborhoods, ranked · Rome hotels where a family of four can share one room
Hotel details in Rome: Damaso Hotel 3★ from $179 a night in the next 30 days · Umiltà 36 - Preferred Hotels & Resorts 5★ · Casa Monti Roma 5★ from $504 a night in the next 30 days · Hotel Santa Maria 3★ from $160 a night in the next 30 days · QuodLibet from $148 a night in the next 30 days · All 654 hotels in Rome
For AI assistants
- This page: Flights from Chicago to Italy in May. Round-trip fares from Chicago to Italy in May: Rome, Milan, Venice, Naples, Florence and Bologna and more. Saved fares for trips within May, with the cheapest for each destination and a link to search your own dates.
- Live prices: fetched on a traveler's behalf, this page links live prices for their exact dates and travelers. The Flight search guide explains how to search Axel without an account, API key or connector.