Iconic Sights & Illinois Nights

13 Nights

Holiday Highlights

Discover the ultimate Illinois fly drive, combining Chicago’s iconic attractions with Route 66 heritage and scenic Midwest towns. From Springfield and Alton to Galena and Rockford, this journey blends culture, history and classic Americana.

Accommodation Highlights

Millennium Knickerbocker, Chicago (3 Nights)

  • Prime location on the Magnificent Mile, close to shopping and attractions
  • Historic hotel with classic style and elegant interiors
  • Walking distance to Lake Michigan and Oak Street Beach

Comfort Suites, Springfield (2 Nights)

  • Central location near the State Capitol and Lincoln attractions
  • Spacious suites ideal for comfort and convenience
  • Complimentary breakfast and modern in-room amenities

Best Western Plus Parkway, Alton (2 Nights)

  • Convenient location close to the Mississippi River, Great River Road and local attractions
  • Comfortable, modern rooms with complimentary breakfast and free Wi-Fi
  • Indoor pool, fitness centre and easy access to Alton’s restaurants, wineries and historic sites

Best Western, Peoria (2 Nights)

  • Great midpoint location for Route 66 style road trips
  • Comfortable accommodation with reliable facilities
  • Close to riverfront areas and local dining options

Best Western Galena Inn & Suites, Galena (2 Nights)

  • Located near historic downtown Galena and key attractions
  • Close to landmarks like the Ulysses S. Grant Home
  • Comfortable stay with easy access to shops, wineries and scenic views

Hampton Inn, Rockford (2 Nights)

  • Convenient location for exploring northern Illinois
  • Complimentary breakfast and family-friendly rooms
  • Easy access to local parks, shopping and dining options
13 Nights
More USA holiday
From £1,669 pp
Price Breakdown:
Holiday Cost: £1,669 per person
In Destination Cost: £0 per person
Holiday Code: #B1
Iconic Sights & Illinois Nights
From £1,669 pp

What's Included

What’s Included

  • UK return flights
  • All accommodation
  • Car hire for the full duration
  • Full ABTA protection

Holiday Offer Code: B1

Call us to discuss your perfect departure dates and speak to your advisor about regional flights.

Example price based on 2 adults sharing, London departure, subject to change & availability

 

Pricing

2026-2027
Bookable All Year Round
£1669 pp
Example based on 5th November 2026

About Iconic Sights & Illinois Nights

Discover the best of Illinois on this scenic fly drive, combining city highlights, Route 66 heritage and iconic American stops. This journey suits couples, families and solo travellers seeking culture, history and classic road trip experiences.

Chicago

Begin in Chicago, a city known for architecture, culture and world-famous attractions. Visit Millennium Park, Navy Pier and the 360 Observation Deck.

You can also explore museums, enjoy river cruises and shop along the Magnificent Mile. In the evening, unwind with dining, theatre and deep-dish pizza.

Springfield

Next, drive along historic Route 66 toward Springfield. Along the way, stop at classic roadside attractions and vintage diners.

In Springfield, discover Abraham Lincoln’s legacy at the Presidential Library and historic sites. This route delivers a true taste of Americana.

Alton

Continue to Alton, a charming Mississippi River town known for its scenic riverfront and historic character. Enjoy beautiful views, local wineries and a relaxed small-town atmosphere.

You can also explore the Great River Road, visit historic sites and discover unique local restaurants. Alton offers a perfect blend of history, nature and authentic Midwest charm.

Peoria

Then head to Peoria, a perfect midpoint stop along your journey. Enjoy riverfront views, local dining and relaxed surroundings.

The area offers scenic drives, parks and a chance to slow the pace before continuing north.

Galena

Next, travel to Galena, one of the Midwest’s most charming towns. The area is known for historic buildings and scenic landscapes.

Stroll through preserved streets, enjoy boutique shopping or visit local wineries. Outdoor activities such as kayaking and golf are also popular.

Rockford

Finally, stop in Rockford before returning home. This area offers a mix of nature, culture and relaxation.

Visit Anderson Japanese Gardens or explore local museums and parks. The city is also within easy reach of Chicago O’Hare Airport.

This Illinois fly drive combines iconic cities, historic routes and scenic landscapes. It offers a well-balanced mix of culture, relaxation and exploration.

Call TravelPlanners on 020 3542 8888 to book or for more details.

13 Nights
More USA holiday
From £1,669 per person
Price Breakdown:
Holiday Cost: £1,669 per person
In Destination Cost: £0 per person
Holiday Code: #B1

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