15 days in Chicago, Italy & Greece Itinerary

15 days in Chicago, Italy & Greece Itinerary

Created using Inspirock trip planner

Plan created by another user. Make it yours
1
Chicago, United States
— Few hours
2
Venice, Italy
— 2 nights
3
Florence, Italy
— 3 nights
4
Rome, Italy
— 1 day
5
Athens, Greece
— 2 nights
6
Oia, Greece
— 5 nights
7
Chicago, United States
— Few hours

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few
hours
Chicago, United States

Chicago ©

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Kick off your visit on the 29th (Tue): explore the landscape on two wheels at Lakefront Trail and then make a trip to Buckingham Fountain.

To find other places to visit, ratings, photos, and other tourist information, you can read our Chicago sightseeing planner.

Madison to Chicago is an approximately 3-hour car ride. You can also drive; or take a bus; or fly. Expect a daytime high around 81°F in June, and nighttime lows around 63°F. Wrap up your sightseeing by early afternoon on the 29th (Tue) to allow time for travel to Venice.

Things to do in Chicago

Parks · Outdoors · Trails
Highlights from your plan
Lakefront Trail ©
Lakefront Trail
Buckingham Fountain ©
Buckingham Fountain

2
nights
Venice, Italy

Venice ©

City of Romance

Virtually unchanged for the last six centuries, Venice is actually a group of islands made famous by a series of canals, bridges, monuments, piazzas, and narrow pedestrian lanes.
Discover out-of-the-way places like Dorsoduro and Cannaregio. Shop till you drop at Mercati di Rialto and T Fondaco Dei Tedeschi. And it doesn't end there: see the interesting displays at Doge's Palace, contemplate in the serene atmosphere at Scuola Grande di San Rocco, admire the landmark architecture of Basilica di San Marco, and make a trip to Basilica di Santa Maria Gloriosa dei Frari.

To find traveler tips, photos, where to stay, and more tourist information, you can read our Venice journey planning tool.

You can fly from Chicago to Venice in 13 hours. Due to the time zone difference, you'll lose 7 hours traveling from Chicago to Venice. In June in Venice, expect temperatures between 81°F during the day and 63°F at night. Wrap up your sightseeing on the 2nd (Fri) to allow time to drive to Florence.

Things to do in Venice

Highlights from your plan
Doge's Palace ©
Doge's Palace
Dorsoduro ©
Dorsoduro
Cannaregio ©
Cannaregio

3
nights
Florence, Italy

Florence ©

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
On the 3rd (Sat), appreciate the history behind Loggia dei Lanzi, get to know the fascinating history of Piazza del Duomo, contemplate in the serene atmosphere at Cathedral of Santa Maria del Fiore, then view the masterpieces at After Art Gallery, then view the masterpieces at Art Gallery Studio Iguarnieri, and finally explore the world behind art at Florence Academy of Fine Arts. Here are some ideas for day two: relax and float downstream with Firenze Rafting, get interesting insight from Tours, then stroll through Easy Living - Spiaggia sull'Arno, and finally view the masterpieces at Clet's Studio.

To find other places to visit, more things to do, reviews, and more tourist information, go to the Florence road trip site.

Traveling by car from Venice to Florence takes 3 hours. Alternatively, you can take a train; or fly. July in Florence sees daily highs of 86°F and lows of 65°F at night. Wrap up your sightseeing on the 5th (Mon) early enough to take a train to Rome.

Things to do in Florence

Highlights from your plan
Florence Academy of Fine Arts ©
Florence Academy of Fine Arts
Cathedral of Santa Maria del Fiore ©
Cathedral of Santa Maria del Fiore
Piazza del Duomo ©
Piazza del Duomo

1
day
Rome, Italy

Rome ©

Eternal City

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
On the 5th (Mon), get interesting insight from Safari d'Arte, look for gifts at Gelateria Panna e Liquirizia, delve into the distant past at Pantheon, then contemplate the long history of St. Peter's Basilica, and finally stroll the grounds of Vatican Necropolis.

For more things to do, other places to visit, ratings, and tourist information, refer to the Rome trip planner.

Getting from Florence to Rome by train takes about 2.5 hours. Other options: drive; or fly. Expect a daytime high around 89°F in July, and nighttime lows around 70°F. Finish your sightseeing early on the 5th (Mon) so you can travel to Athens.

Things to do in Rome

Side Trip

Highlights from your plan
Pantheon ©
Pantheon
St. Peter's Basilica ©
St. Peter's Basilica
Vatican Necropolis ©
Vatican Necropolis

2
nights
Athens, Greece

Athens ©

The Birthplace of Democracy

One of the world's most ancient cities, Athens remains Europe's undisputed historical and cultural capital.
Explore hidden gems such as Temple of Hephaestus and Temple of Athena Nike. Get some cultural insight at Acropolis of Athens and Plaka. Next up on the itinerary: get engrossed in the history at Acropolis Museum, take a stroll around Stavros Niarchos Foundation Cultural Centre, pause for some photo ops at Erechtheion, and take your sightseeing to a higher altitude at Mount Lycabettus.

To find maps, other places to visit, ratings, and other tourist information, read Athens trip itinerary planner.

Traveling by flight from Rome to Athens takes 6 hours. Alternatively, you can do a combination of car and ferry; or do a combination of train, ferry, and bus. The time zone changes from Central European Standard Time to Eastern European Standard Time, which is usually a 1 hour difference. In July in Athens, expect temperatures between 91°F during the day and 75°F at night. Wrap up your sightseeing on the 8th (Thu) early enough to travel to Oia.

Things to do in Athens

Historic Sites · Shopping · Neighborhoods · Parks

Side Trip

Highlights from your plan
Temple of Hephaestus ©
Temple of Hephaestus
Acropolis of Athens ©
Acropolis of Athens
Acropolis Museum ©
Acropolis Museum

5
nights
Oia, Greece

Oia ©
Every day hundreds of visitors come to Oia just to experience its sunsets.
Your itinerary includes some good beach time at Red Beach and Vourvoulos Beach. Visiting Santorini Sailing and Eros Beach will get you outdoors. You'll find plenty of places to visit near Oia: Akrotiri (Akrotiri & La Ponta), Megalochori (Venetsanos Winery & Gavalas Winery) and Artemis Karamolegos Winery (in Exo Gonia). And it doesn't end there: awaken your taste buds at Santorini Tours, see the interesting displays at Cultural Village, view the masterpieces at Mnemossyne Gallery, and explore the historical opulence of Castelli of Pyrgos.

Start your trip to Oia by creating a personalized itinerary on Inspirock.

Traveling by flight from Athens to Oia takes 5 hours. Alternatively, you can do a combination of car and ferry; or do a combination of ferry and taxi. When traveling from Athens in July, plan for slightly colder days in Oia, with highs around 86°F, while nights are about the same with lows around 74°F. Wrap up your sightseeing on the 13th (Tue) early enough to travel to Chicago.

Things to do in Oia

Wineries · Outdoors · Parks · Beaches

Side Trips

Highlights from your plan
Santorini Sailing ©
Santorini Sailing
Venetsanos Winery ©
Venetsanos Winery
Santorini Tours ©
Santorini Tours

few
hours
Chicago, United States

Chicago ©

Windy City

Start off your visit on the 13th (Tue): explore the landscape on two wheels at Lakefront Trail.

To see photos, maps, where to stay, and tourist information, you can read our Chicago trip planning app.

Getting from Oia to Chicago by flight takes about 17.5 hours. You'll gain 8 hours traveling from Oia to Chicago due to the time zone difference. Traveling from Oia in July, plan for little chillier nights in Chicago, with lows around 67°F. Wrap up your sightseeing by early afternoon on the 13th (Tue) to allow enough time to drive back home.

Things to do in Chicago

Parks · Outdoors · Trails
Highlights from your plan
Lakefront Trail ©
Lakefront Trail

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