A modern bridge with a reflection in the water, surrounded by historic buildings and tall skyscrapers.
Photo by Leo Li
Open Photo by Leo Li

Great Lakes Romantic Holidays

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Top Romantic holiday packages in Great Lakes

Price found within the past 48 hours. Click for updated prices.
  • 28 Oct - 2 Nov

    Hotel Saint Clair- Magnificent Mile + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    8.4/10 - Very good (2,092 reviews)
    "My stay at the St. Clair Hotel was overall a good experience. The room was clean, cozy, and exactly as described. Everything was well maintained, and the hotel was in a convenient location. There were just a couple of things that could be improved. The room did not include bottled water, and it wasn’t clear whether water was available for purchase or if guests needed to request it. It would be helpful if the hotel clarified this for future guests. Also, I also ask about a crib for my..."
    Reviewed August 4, 2026
    Return London (LON) - Chicago (ORD)
    LHR - ORDDirect ORD - LHR1 stop
    £1,338
    £956
    per traveller
    found 1 day ago
    Hotel Saint Clair- Magnificent Mile
  • 8 Oct - 13 Oct

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.4/10 - Exceptional (2,641 reviews)
    "Everything was great."
    Reviewed August 4, 2026
    Return London (LGW) - Chicago (ORD)
    LGW - ORD1 stop ORD - LGW1 stop
    Save 100% on your flight
    £2,296
    £1,576
    per traveller
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • 8 Oct - 13 Oct

    Eurostars Magnificent Mile + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.0/10 - Wonderful (3,780 reviews)
    Return London (LGW) - Chicago (ORD)
    LGW - ORD1 stop ORD - LGW1 stop
    Save 100% on your flight
    £2,334
    £1,633
    per traveller
    found 1 day ago
    Eurostars Magnificent Mile
  • 27 Sept - 3 Oct

    TOOR Hotel Toronto, part of JdV by Hyatt + Flight

    Downtown Toronto
    6 nights
    4.0 star property
    9.4/10 - Exceptional (916 reviews)
    "Good hotel close to Eaton Center. The management and staff were not helpful at all; many of them did not seem well-rounded on the job."
    Reviewed August 4, 2026
    Return London (LGW) - Toronto (YYZ)
    LGW - YTZ1 stop YTZ - LGW1 stop
    Save 100% on your flight
    £1,356
    £960
    per traveller
    found 1 day ago
    TOOR Hotel Toronto, part of JdV by Hyatt
  • 28 Oct - 2 Nov

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    5 nights
    5.0 star property
    9.6/10 - Exceptional (1,970 reviews)
    Return London (LON) - Chicago (ORD)
    LHR - ORDDirect ORD - LHR1 stop
    £2,130
    £1,545
    per traveller
    found 1 day ago
    Trump International Hotel & Tower Chicago

Discover the most popular places to visit in Great Lakes

What to do in Great Lakes

Top Romantic Great Lakes Hotels

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

How to find a romantic Great Lakes holiday

How can I find the best Great Lakes vacation packages for couples?

Use our easy-to-use holiday search tools to plan your most-romantic getaway to Great Lakes. Choose a hotel suite with an on-trend bathtub with a big view. Choose a stylish hire car with the top down to woo your heart. Choose candlelit cocktails on the shoreline, a horse ride by moonlight or a dolled-up night at the casino.

Can I book cheap Great Lakes romantic holidays for two?

Get wallet-friendly away-from-it-all romantic accommodation at Expedia, so you have more kitty to spend on romantic activities. We have cheap romantic holidays to Great Lakes that start from £956. Prices and availability are subject to change. Additional terms may apply.

What should I think about when booking a Great Lakes romantic getaway?

The most romantic holidays are about building memories, about dancing and dining and keeping the spark alive. These are moments to level up the luxury – use the star filter to find the best of the best, maybe even tick the business-class flights filter to make the journey part of the adventure.

What should I look for in a luxury romantic holiday to Great Lakes?

Spoil yourselves with a few luxuries on your romantic trip away. You can use our filters to add that extra touch of romance to your holiday: glamorous spas, divine private dining, exquisite room service.

Can I book a romantic hot-tub holiday in Great Lakes?

What’s more romantic than a hot tub under the stars, together? Add a glass of fizz, a gorgeous view and Cupid’s arrow and you’re good. To find accommodation with bubbles, use our dedicated hot-tub filter.

How can I find romantic holidays for couples in Great Lakes that are all inclusive?

Enjoying an all-inclusive holiday means you can really indulge your appetites together – with the promise of no awkward arguments about splitting the bill. Simply use our all-inclusive filter to see what romantic options are available.

Can I book a romantic trip to Great Lakes with free cancellation and/or flexible dates?

Even the best laid plans fall through sometimes. Make sure you’re not caught out – using our filters to find free cancellation accommodation. Just make sure you check the all-important small print.

Why should I book my Great Lakes romantic holiday with Expedia?

At Expedia, we know the not-so-secret ingredients to the perfect romantic holiday. Our handy filters help you search a huge range of options and book a holiday that gets your hearts racing.