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Itinerary
New York & Chicago Twin
New York & Chicago 8 Days
Highlights:
- New York City
- Chicago
- New York: Go City Explorer Pass
- Chicago Go City Explorer Pass
Prices Include:
Accommodation
Internal Flights
International Flights
Tickets & Activities
From £1,289 pp
Itinerary # OMC4103
- Best For:
- Adult Friendly
- Speciality Tours
- Twin Centre
- Best For:
- Adult Friendly
- Speciality Tours
- Twin Centre
From £1,289 pp
Itinerary # OMC4103
Highlights:
- New York City
- Chicago
- New York: Go City Explorer Pass
- Chicago Go City Explorer Pass
Prices Include:
- Accommodation
- Internal Flights
- International Flights
- Tickets & Activities
"Our most complete tour of Argentina for an overview of this diverse country, including Patagonia, the Iguazu Falls and much more!"
Pair two American greats on a 7-night adventure – exploring the bustling cityscape of New York and the enchanting heart of the Midwest in Chicago.
Itinerary
Chicago & Milwaukee Twin
Chicago & Milwaukee, 9 Days
Highlights:
- Chicago
- Wisconsin
- Skydeck Chicago Admission Ticket
- Chicago Mob and Crime Bus Tour
- Chicago River 90-Minute Architecture Tour
- + 3 more
Prices Include:
5+ Tickets & Activities- Accommodation
- International Flights
Train
From £1,359 pp
Itinerary # OMC4222
- Best For:
- Adult Friendly
- Train Journeys
- Twin Centre
- Best For:
- Adult Friendly
- Train Journeys
- Twin Centre
From £1,359 pp
Itinerary # OMC4222
Highlights:
- Chicago
- Wisconsin
- Skydeck Chicago Admission Ticket
- Chicago Mob and Crime Bus Tour
- Chicago River 90-Minute Architecture Tour
- + 3 more
Prices Include:
- 5+ Tickets & Activities
- Accommodation
- International Flights
- Train
"Our most complete tour of Argentina for an overview of this diverse country, including Patagonia, the Iguazu Falls and much more!"
Indulge in Chicago’s mob history and striking architecture and Milwaukee’s brewing history on this 9-day adventure with Amtrak train connections.
Itinerary
Chicago & Cincinnati
Chicago & Cincinnati, 8 Days
Highlights:
- Chicago
- Ohio
- Chicago CityPASS®
- Cincinnati: Ohio River Cruise with Buffet Dinner
- Ultimate Queen City Underground Tour
Prices Include:
- Accommodation
- Internal Flights
- International Flights
- Tickets & Activities
From £1,379 pp
Itinerary # OMC4221
- Best For:
- Speciality Tours
- Twin Centre
- Best For:
- Speciality Tours
- Twin Centre
From £1,379 pp
Itinerary # OMC4221
Highlights:
- Chicago
- Ohio
- Chicago CityPASS®
- Cincinnati: Ohio River Cruise with Buffet Dinner
- Ultimate Queen City Underground Tour
Prices Include:
- Accommodation
- Internal Flights
- International Flights
- Tickets & Activities
"Our most complete tour of Argentina for an overview of this diverse country, including Patagonia, the Iguazu Falls and much more!"
Explore Chicago’s skyline and museums, then uncover Cincinnati’s underground secrets and beer heritage on this 8-day twin-city journey.
Itinerary
Chicago & Detroit
Chicago & Detroit 8 Days
Highlights:
- Chicago
- Detroit
- Big Bus Chicago: Hop-On Hop-Off Sightseeing Tour by Open-Top Bus
- Skydeck Chicago Admission Ticket
- Chicago Buffet Lunch Cruise on Lake Michigan
- + 2 more
Prices Include:
- 5+ Tickets & Activities
- Accommodation
- Internal Flights
- International Flights
From £1,499 pp
Itinerary # OMC4220
- Best For:
- Heritage Tours
- Speciality Tours
- Twin Centre
- Best For:
- Heritage Tours
- Speciality Tours
- Twin Centre
From £1,499 pp
Itinerary # OMC4220
Highlights:
- Chicago
- Detroit
- Big Bus Chicago: Hop-On Hop-Off Sightseeing Tour by Open-Top Bus
- Skydeck Chicago Admission Ticket
- Chicago Buffet Lunch Cruise on Lake Michigan
- + 2 more
Prices Include:
- 5+ Tickets & Activities
- Accommodation
- Internal Flights
- International Flights
"Our most complete tour of Argentina for an overview of this diverse country, including Patagonia, the Iguazu Falls and much more!"
Explore Chicago’s skyline and mobster history, then dive into Detroit’s Motown and auto legacy on this 8-day adventure.
Itinerary
Midwest USA to the Rockies
Chicago to Denver, 13 Days
Highlights:
- Chicago
- South Dakota
- Colorado
- Chicago CityPASS®
- Self-Guided Scavenger Hunt: Rock and Roll Through Sioux Falls
- + 3 more
Prices Include:
- 5+ Tickets & Activities
- Accommodation
Car Hire- International Flights
From £1,819 pp
Itinerary # OMC4203
- Best For:
- Road Adventures
- Nature Explorations
- Speciality Tours
- Best For:
- Road Adventures
- Nature Explorations
- Speciality Tours
From £1,819 pp
Itinerary # OMC4203
Highlights:
- Chicago
- South Dakota
- Colorado
- Chicago CityPASS®
- Self-Guided Scavenger Hunt: Rock and Roll Through Sioux Falls
- + 3 more
Prices Include:
- 5+ Tickets & Activities
- Accommodation
- Car Hire
- International Flights
"Our most complete tour of Argentina for an overview of this diverse country, including Patagonia, the Iguazu Falls and much more!"
Journey from Chicago to Denver on a 13-day Midwest to the Rockies adventure.
Itinerary
Half Route 66
Half Route 66, 17 Days
Highlights:
- Chicago
- Missouri
- Route 66
- Oklahoma
- Texas
- + 9 more
Prices Include:
- 5+ Tickets & Activities
- Accommodation
- Car Hire
- International Flights
From £3,049 pp
Itinerary # OMC4176
- Best For:
- Road Adventures
- Heritage Tours
- Speciality Tours
- Best For:
- Road Adventures
- Heritage Tours
- Speciality Tours
From £3,049 pp
Itinerary # OMC4176
Highlights:
- Chicago
- Missouri
- Route 66
- Oklahoma
- Texas
- + 9 more
Prices Include:
- 5+ Tickets & Activities
- Accommodation
- Car Hire
- International Flights
"Our most complete tour of Argentina for an overview of this diverse country, including Patagonia, the Iguazu Falls and much more!"
Travel the Half Route 66 from Chicago to Albuquerque, hitting St. Louis, Tulsa, Amarillo, and more.
Itinerary
Classic Route 66
Classic Route 66, 22 Days
Highlights:
- Chicago
- Missouri
- Texas
- New Mexico
- Arizona
- + 11 more
Prices Include:
- 5+ Tickets & Activities
- Accommodation
- Car Hire
- International Flights
From £3,629 pp
Itinerary # OMC4177
- Best For:
- Road Adventures
- Heritage Tours
- Speciality Tours
- Best For:
- Road Adventures
- Heritage Tours
- Speciality Tours
From £3,629 pp
Itinerary # OMC4177
Highlights:
- Chicago
- Missouri
- Texas
- New Mexico
- Arizona
- + 11 more
Prices Include:
- 5+ Tickets & Activities
- Accommodation
- Car Hire
- International Flights
"Our most complete tour of Argentina for an overview of this diverse country, including Patagonia, the Iguazu Falls and much more!"
Hit play on adventure and travel along the iconic Route 66 from Chicago to LA.
1 - 7 of 7 Deals
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Why we are the UK's #1 Independent Florida specialists
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Book as far
ahead as 2027
ahead as 2027
As an independent travel company, we can offer you packages up to 36-months in advance.
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Access to over 2,500
exact homes across
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We’re proud to have been awarded Travel For All award at the Travel Weekly Globes 2024 & 2025.
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Let’s find your once-in-a-lifetime! Somewhere that makes everyone from grandparents to grandchildren feel like big kids. A place where “finally” is said aloud. This is where bucket lists are re-written. Where from your first quote until your flight home, you can feel the Ocean Difference with personalised quotes, bespoke itineraries, and award-winning service. We are your holiday shapers and memory makers for dreams of every size, including 24/7 support for all your needs abroad. Get in touch today for everyday fairytales found only with Ocean Florida.
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We have an amazing support team based in Orlando who are available 24/7 to help you with any questions or queries you might have during your holiday.
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FAQ's
Chicago Deals
Chicago Deals
- Handpicked deals put together by experts
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- Book your holiday up to 18 months ahead
Whether you're looking for a week in the 'Windy City' or just a few nights before heading to another destination, let our Chicago packages show you the way. Our collection of deals and packages to Chicago have been expertly created with care and attention to detail, ensuring everything works just right.
Embark on an adventure to Chicago you’d never expect possible. Thanks to a dedicated team, with a passion for creating exceptionally packaged holidays and bespoke deals, you’ll find that it’s easier than ever to explore Chicago just the way you want to.
Amongst the largest cities in the U.S. we’ll take you on a journey to every corner of Chicago making sure you never miss a thing, if you want to visit the iconic Navy Pier in the morning before spending the day at Lincoln Park Zoo with your family, we’ll make it easily possible.
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Itineraries across
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