Cobb Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
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Your Cobb Vacation
From its highlights to its hidden treasures, this city is best experienced with a Cobb vacation package. Find a place to stay in Downtown Mineral Point, which is great for bars and pubs, dining and history. Make sure to do some sightseeing during your trip to Cobb. Blackhawk Lake Recreation Area and Beach at Black Hawk Lake Recreation Area are some favorite places to check out. Stop daydreaming and start traveling. Browse the range of options on Expedia today and finally put your Cobb vacation plans in motion!
Top Cobb vacation deals
- Sheraton Grand Chicago Riverwalk
Dec 19 - Dec 23Sheraton Grand Chicago Riverwalk + Flight
Downtown Chicago4 nights4.0 star property8.6/10 - Excellent (1,875 reviews)Roundtrip • Hamilton (YHM) - Chicago (ORD)YHM - ORD • 1 stop ORD - YHM • 1 stopCA $2,739CA $1,191found 1 day agoper traveller - Kimpton Gray Hotel by IHG
Dec 27 - Jan 2Kimpton Gray Hotel by IHG + Flight
Downtown Chicago6 nights4.5 star property9.4/10 - Exceptional (1,002 reviews)Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - ORD • Nonstop ORD - YTZ • Nonstop - Park Hyatt Chicago
Dec 27 - Jan 2Park Hyatt Chicago + Flight
Downtown Chicago6 nights5.0 star property9.6/10 - Exceptional (1,001 reviews)"Given the price point and other reviews, we came here expecting a luxury stay similar to the Waldorf Astoria, Four Seasons, and Peninsula, which are some of our favorite properties to stay at. However, everything from the service and cleanliness to the ambiance of the entrance and lobby and the amenities (other than the gym, which was excellent) is best described as an upgraded version of an average Hilton, Hyatt, or Marriott. For example, there was a hair in the bed. When we reported it, the..."Reviewed November 4, 2026Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - ORD • Nonstop ORD - YTZ • Nonstop - The Peninsula Chicago
Dec 27 - Jan 2The Peninsula Chicago + Flight
Downtown Chicago6 nights5.0 star property9.8/10 - Exceptional (1,008 reviews)Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - ORD • Nonstop ORD - YTZ • Nonstop - Trump International Hotel & Tower Chicago
Dec 24 - Dec 28Trump International Hotel & Tower Chicago + Flight
Downtown Chicago4 nights5.0 star property9.6/10 - Exceptional (2,077 reviews)"Beautiful hotel situated perfectly for most downtown Chicago activities. Attentive staff and amazing views from our 14th floor lake view room. This stay has been on my bucket list for awhile. This hotel experience did not disappoint"Reviewed November 6, 2026Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - ORD • Nonstop ORD - YTZ • NonstopCA $2,457CA $1,902found 1 day agoper traveller
Cobb Hotel Deals
Holiday Inn Express and Suites-Platteville by IHG
Holiday Inn Express and Suites-Platteville by IHG"Walkable to restaurants. Friendly staff. Cookies in the afternoon!"
"Free on demand coffee in the lobby. Very clean and maintained."
Best Western Dodgeville Inn & Suites
Best Western Dodgeville Inn & Suites
"The room was spotless and the beds were very comfortable. The breakfast was continental and not much there but there was a waffle maker which was great. I slept well. The two things I would change would be to use a different scent for the air freshener, which had a weird and unpleasant scent, and to clean the entrance glass door, which was very smudged and dirty and made a negative first impression. Those are small changes which would not cost much."
Quality Inn & Suites Belmont - Platteville
Quality Inn & Suites Belmont - Platteville"Thank you!"
"We really enjoyed our stay. The staff are very friendly and helpful. The rooms are clean. Amenities are older but kept up nicely. We will go back"
Frequently Asked Questions
How much does a Cobb vacation package cost?
You can pick up a vacation package to this destination from CA $1,191 on Expedia. However, how much your vacation to Cobb costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Cobb?
If you're hoping to book a cheap Cobb vacation package, consider visiting in January, February and April. You'll usually find lower prices on flights and accommodations during these months — ideal for travellers wishing to save money.
How many days is enough for Cobb?
Typically, a handful of days is enough to tick off the top sights during your Cobb vacation. However, if you want to have more time to rest or go on day tours, think about extending your itinerary.
How to find the best Cobb package deals?
Landing a cheap Cobb package deal is a breeze with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget range, add a couple of filters and browse what's available. You can customize your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to view the most economical Cobb package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Cobb vacation as a package?
You can enjoy significant savings on your Cobb break by booking a personalized vacation package. Check the "Package" heading, then enter your destination and travel dates to see some great hotel and flight prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Cobb?
If you've got your Cobb travel dates confirmed, book as early as you can to grab some terrific deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are perfect for quick escapes.
How to plan a trip to Cobb?
- Choose the ideal time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to go to Cobb.
- Budget wisely: Besides the cost of your stay, you'll need to consider other expenses too. These include flights, transportation and food. Also, put aside some extra funds for unexpected costs that may come up during your trip to Cobb.
- Decide your trip length: Consider how long you want to spend discovering Cobb. Plan your days so you can get to all the activities and attractions you're interested in without rushing.
- Bundle your accommodations and airfare: After you've settled on your trip dates and duration, book the ideal Cobb vacation package for you.