Cambridge Holidays
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- Better togetherSave up to S$1,300 when you book a flight and hotel together*
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Cambridge Flight & Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
S$2,219
per person
8 Nov - 12 Nov
found 20 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
My Labor Day weekend stay at Trump International Hotel & Tower Chicago was exceptional in every regard, marked by refined service, remarkable amenities, and a level of hospitality that felt both genuine and elevated. From the moment I arrived, the staff set a distinguished tone, greeting me with champagne and ensuring every detail of my visit was handled with care. The concierge team was attentive and polished, and throughout my stay I felt consistently supported by a standard of service that exceeded expectations.
Room 2791 offered a breathtaking view of the city, with floor‑to‑ceiling windows framing Chicago’s skyline in a way that felt both serene and spectacular. The terrace added an unforgettable dimension, providing a private space to enjoy the city’s energy from above while still feeling completely at ease. Room service was prompt, beautifully prepared, and consistently excellent, enhancing the comfort of the stay.
The spa and wellness facilities were equally impressive. Ashanti, Christian, and Byron delivered warm, professional service that made each visit feel personal, and my massage therapist provided a treatment that was both restorative and skillfully executed. The sauna, steam room, and gym were immaculate, calming, and thoughtfully maintained, offering a perfect balance of relaxation and rejuvenation. Pablo also stood out for his gracious and attentive service.
This stay left a lasting impression, and I will be making Trump Hotels a part of future travels.✨
Reviewed on 18 Sept, 2026
Top hotels in Cambridge
The Madison Concourse Hotel and Governor's Club
1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
S$174
20 Sept - 21 Sept
includes taxes & fees
Best Western Plus InnTowner Madison
2424 University Avenue Madison WI
Fully refundableReserve now, pay when you stay
S$205
4 Oct - 5 Oct
includes taxes & fees
Motel 6 Madison, WI - East
4202 E Towne Blvd Madison WI
Fully refundableReserve now, pay when you stay
S$66
11 Oct - 12 Oct
includes taxes & fees
6.4/10 (1,027 reviews)
"Parking was good. Room was clean"
Reviewed on 18 Sept, 2026
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.
Stay near popular Cambridge attractions
Lake Ripley Park Beach
Lake Ripley Park Beach features a sandy shoreline with clear, shallow waters ideal for families. Enjoy swimming, tennis courts, or disc golf while using the well-maintained picnic shelters.
Cambridge Winery
8.8/10 (3 reviews)
Savour boutique wines from Wisconsin, California, and New York at this sophisticated tasting destination. Relax in the venue with large windows or enjoy the wrap-around deck while sampling wines paired with artisanal small plates.
Cam-Rock Park Area
Sprawling across 575 acres between Cambridge and Rockdale, CamRock Park offers premier trails for mountain biking, hiking, and skiing. Explore restored prairies and wooded areas, or launch a kayak on Koshkonong Creek.
Hinchley's Dairy Farm
This family-owned Wisconsin dairy farm offers hands-on tours where you can milk cows and bottle-feed calves. Experience modern farming with robotic milkers and tractor-driven hayrides from April to October.
Lake Ripley
Commune with nature and explore the great outdoors at Lake Ripley during your travels in Lake Ripley. Amble around the area's lakeside or experience its entertainment choices.
Dancing Goat Distillery
Wisconsin's first open-air Kentucky-style rickhouse towers five stories high at Dancing Goat Distillery. Sample premium spirits in the tasting room or craft your own bottle at their unique Gin Academy.
Cambridge Historic School Museum
Step back in time at this 1906 schoolhouse museum showcasing Cambridge's educational heritage. Explore the recreated vintage classroom and local veterans' tributes in this charming historical time capsule.
Hope Lake
Commune with nature and explore the great outdoors at Hope Lake during your travels in Cambridge. Wander the lakeside and parks while you're in the area.
Frequently asked questions
How much does a Cambridge holiday package cost?
You can snap up a holiday package to this destination from S$854 on Expedia. But how much your holiday to Cambridge costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Cambridge?
To pick up cheap Cambridge holiday packages, plan your trip outside of peak periods such as public holidays. You'll generally find better availability and lower prices for flights and hotels.
How many days is enough for Cambridge?
We recommend planning a Cambridge holiday for at least 2 days. This will give you enough time to check off top attractions such as Lake Ripley Lanes and Lake Ripley Park Beach, as well as check out neighbourhoods like Rockdale and Utica. You could even squeeze in a day trip or two from Cambridge.
Is it worth booking a holiday package to Cambridge?
Popular for its watersports, mountain biking and cycling, a Cambridge holiday is a hit with all kinds of visitors. Be sure to visit main sights like Lake Ripley Park Beach and Cam-Rock Park Area, and consider renting a car for day trips to experience even more.
How to find the best Cambridge package deals?
Use Expedia's filters to find some unbeatable Cambridge package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Cambridge package deals in the off-season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your holiday package as early as possible.
Is it cheaper to book a Cambridge holiday as a package?
Expedia holiday packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll generally land a better deal than booking each component separately. And you'll still have the freedom to create a tailored Cambridge holiday by choosing your favourite type of stay, airline and car class.
When to book a holiday package to Cambridge?
If you've got your Cambridge holiday dates confirmed, book as early as you can to snap up some terrific deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Cambridge?
- Pick your travel dates: What you plan to do in Cambridge and your favourite season can help you decide when to go.
- Set your budget: Consider costs such as food, flights and transportation when calculating how much to put aside for your trip to Cambridge. Then, select a hotel that fits your budget, whether that's a wallet-friendly stay or a swankier getaway.
- Work out your trip length: Consider how long you'd like to spend exploring Cambridge. Plan your days so you can get to all the activities and attractions you're interested in without rushing.
- Combine your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to pick a Cambridge holiday package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
