Vacations w/ Airfare, Hotel & Tours to Italy from ORD - Chicago

Italy is a traveler's paradise, with its stunning landscapes, rich history, and delicious cuisine. From the ancient ruins of Rome to the picturesque canals of Venice, there is something for everyone to enjoy. The vibrant cities offer a mix of art, culture, and fashion, while the countryside is dotte... read more

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From St. Paul's to St. Peter's: 12 days from London to Rome

Spend two nights in London, two nights in Paris with guided tours, enjoy another two nights in Lucerne, Switzerland with tours, stop by Verona on your way to Venice, tour through Florence next, stop by the landmark the Leaning Tower of Pisa, and finally spend your last two nights touring through Rome.

From
ORD $3,767 * Per Person

11 Nights

2 People

* Escorted vacation is round-trip based on 2 travelers from Chicago Ohare Intl (ORD). Includes airfare & airport taxes, transfers, hotels, transportation, meals & tours. Additional baggage charges may apply.

The Jewels of Southern Italy: Rome, Sicily, Calabria & Sorrento

Vacation through the enchanting landscapes and renowned landmarks of southern Italy on this guided tour that spans multiple cities. Commence your journey in the historic city of Rome, followed by an overnight ferry ride to the picturesque island of Sicily. Continue your exploration through the region of Calabria, and finally, bask in the coastal beauty of the Sorrentine Peninsula. With the ease of having airfare, transportation, lodging, and guided tours all meticulously arranged, this 9-night expedition offers the Italian getaway you've always envisioned.

From
ORD $2,963 * Per Person

9 Nights

2 People

* Escorted vacation is round-trip, per person, based on 2 travelers from Chicago Ohare Intl (ORD). Includes air, airport taxes, transfers, hotels, sightseeing, transportation, breakfast and more. Additional baggage charges may apply. Rates are available for 1 to 9 travelers.

Splendors of Italy

Explore the highlights of Italy, from towering cathedrals and medieval towers to Renaissance art, ancient ruins, and decadent wine. Enjoy vacationing through Siena, Montecatini, Rome, Florence, and more on this amazing, well-rounded Italian experience.

From
ORD $3,197 * Per Person

8 Nights

2 People

Tourist visiting the Colosseum in Rome, Italy

Simply Rome

Walking through Rome is like walking through a postcard. From St. Peter's Basilica to the Colosseum, experience the iconic sites of the Eternal City! Visit the Trevi Fountain, walk the Spanish Steps, and indulge in pizza, gelato, and other Italian favorites. This affordable vacation allows you to travel to Rome for less, so you'll have more to spend on souvenirs!

From
ORD $1,044 * Per Person

4+ Nights

2 People

* Vacation is round-trip, per person, based on 2 travelers from Chicago Ohare Intl (ORD). Includes air, airport taxes, hotel and daily breakfast. Additional baggage charges may apply. Rates are available for 1 to 9 travelers.

Enjoy Italian coffee on a quaint terrace

Explore Rome City

Explore Rome in all its glory by visiting ancient ruins, tossing a coin into the Trevi Fountain for a wish, sipping the richest cappuccinos, and wandering through a city rich in culture, history, and magnificence. With monuments, landmarks, museums, art, and gardens available to guests, see as much of the Eternal City as you can in all its splendor.

From
ORD $1,536 * Per Person

4+ Nights

2 People

* Vacation package is round-trip, per person, based on 2 people traveling. Includes airfare & airport taxes, hotels, transfers and breakfast daily. Additional baggage charges may apply.

Best of Italy

Journey through Italy on this once-in-a-lifetime escorted vacation! Visit the historical cities of Rome, Florence, Milan, Venice, and Genoa, feast your eyes on the coast from Capri, Sorrento, and Cinque Terre, and see sites like Pompeii, the Leaning Tower of Pisa, and St. Francis Basilica in Assisi. With a special stop in Lugano, Switzerland, this Italian dream vacation is packed with extraordinary beauty from start to finish.

From
ORD $4,498 * Per Person

13 Nights

2 People

* Escorted vacation is round-trip, per person, based on 2 travelers from Chicago Ohare Intl (ORD). Includes air & airport taxes, hotels, transportation, tours, breakfast daily and more. Additional baggage charges may apply.

Paris & Rome

Tour two European cities known for romance, art, culture, food, and history. Begin in Paris and wander through its cobblestone streets, visit world-class museums like the Louvre and Musee d'Orsay, and enjoy a picnic at Luxembourg Gardens. Fly to Rome and wrap yourself in all things Italian, from pasta to ancient Roman ruins like the Colosseum.

From
ORD $2,097 * Per Person

6+ Nights

2 People

* Vacation is round-trip, per person, based on 2 travelers from Chicago Ohare Intl (ORD). Includes airfare & airport taxes, hotels, tours and breakfast daily. Additional baggage charges may apply.

Escorted Journey: Rome's Highlights & Tuscan Villa Charm

Discover the best of Italy with this escorted vacation. Stay at the historic Villa Casagrande in the heart of Tuscany, nestled among rolling hills, lush vineyards, and fragrant olive groves. From here, you will explore enchanting medieval towns, tour wineries, and discover cultural gems. This journey also includes hands-on cooking classes, wine tastings, and expert led tours of iconic cities like Florence, Venice, and more.

From
ORD $3,391 * Per Person

8 Nights

2 People

* Escorted vacation is round-trip, per person, based on 2 travelers. Includes air & airport taxes, transfers, hotels, sightseeing, transportation, daily breakfast and more. Additional baggage charges may apply.

Explore Rome, Sorrento & Positano

Journey through ancient Rome, unwind on the sun-drenched beaches of Sorrento, and immerse yourself in the picturesque beauty of Positano — all at leisure with an included rental car. Discover Italy with ease and adaptability while enjoying countless adventures at every corner.

From
ORD $2,015 * Per Person

6+ Nights

2 People

* Vacation is round-trip, per person, based on 2 travelers from Chicago Ohare Intl (ORD). Includes air & airport taxes, transfer, hotels, rental car and breakfast daily. Additional baggage charges may apply. Rates are available for 1 to 9 travelers.

Solo Travel: Journey to Rome

Explore Rome your way! Your airfare and accommodation are all sorted out, so now you have the pleasure of choosing ways to fill your days! From visiting the Colosseum, to people watching at Piazza Navona, to tossing a coin into the Trevi Fountain, your Rome solo adventure is sure to be incredible.

From
ORD $2,107 * Per Person

4+ Nights

1 People

* Vacation package is round-trip, per person, based on 1 person traveling from Chicago Ohare Intl (ORD). Includes airfare & airport taxes, hotels, transfers and breakfast daily. Additional baggage charges may apply.

Marvel at historic villages in Umbria, Italy

Rustic Umbria with Rome

See Rome and Umbria on this 7-night getaway! Spend 5 nights in Italy's green heart of Umbria, with rolling green hills as far as the eye can see. Then make your way to Rome for 2 nights, Italy's historic and vivacious capital city. Enjoy wine tastings, city tours and more!

From
ORD $2,121 * Per Person

7 Nights

2 People

* Vacation package is round-trip, per person, based on 2 travelers. Package includes airfare & airport taxes, car, accommodations, tours, departure transfer and breakfast daily. Additional baggage charges may apply.

Off-The-Beaten-Path: Gems of Western Europe

Discover the true essence of 'off-the-beaten-path' with a Western Europe adventure, including Paris and London, plus the potential addition of Rome and/or Dublin should you opt for the 9- or 12-night getaway. Embrace each city's secret treasures with unique tours and ample free time to explore renowned attractions independently.

From
ORD $2,777 * Per Person

6+ Nights

2 People

* Vacation is round-trip, per person, based on 2 travelers from Chicago Ohare Intl (ORD). Includes air, airport taxes, transfers, hotels, rail, tours and daily breakfast. Additional baggage charges may apply. Rates are available for 1 to 9 travelers.

Off-The-Beaten-Path: Paris & Rome for Foodies

Prepare for an extraordinary exploration of Paris and Rome's culinary delights with two exclusive gastronomy tours! Begin your gastronomic adventure in the City of Love, where you'll immerse yourself in the Parisian culinary landscape through an enchanting guided food tour led by a knowledgeable local chef. In the Eternal City of Rome, you'll have the chance to uncover the hidden culinary treasures with the guidance of a passionate local expert.

From
ORD $2,834 * Per Person

6+ Nights

2 People

* Vacation is round-trip, per person, based on 2 travelers from Chicago Ohare Intl (ORD). Includes air, airport taxes, transfers, hotels, tours and breakfast. Additional baggage charges may apply. Rates are available for 1 to 9 travelers.

Hilton Luxury: London & Waldorf Astoria Rome

Experience unparalleled luxury at the esteemed Waldorf Hilton in London and the 5-star Rome Cavalieri, A Waldorf Astoria Hotel. Delve into iconic landmarks and lesser-known treasures with private tours, elevating your journey with personalized attention. Explore London's Big Ben and Rome's Colosseum, immersing yourself in the highlights of these magnificent cities.

From
ORD $3,322 * Per Person

6+ Nights

2 People

* Vacation is round-trip, per person, based on 2 travelers from Chicago Ohare Intl (ORD). Includes air, airport taxes, hotels, tours and daily breakfast. Additional baggage charges may apply. Rates are available for 1 to 9 travelers.