Boulder Hill Vacations from $318

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The Latest Boulder Hill Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Dec 22 - Dec 24

    Sheraton Grand Chicago Riverwalk + Flight

    Downtown Chicago
    2 nights
    4.0 star property
    8.6/10 - Excellent (1,875 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $1,271
    $318
    per traveler
    found 1 day ago
    Sheraton Grand Chicago Riverwalk
  • Jan 7 - Jan 13

    THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel + Flight

    Downtown Chicago
    6 nights
    4.0 star property
    8.6/10 - Excellent (1,003 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $718
    $415
    per traveler
    found 1 day ago
    THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
  • Dec 24 - Dec 29

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.4/10 - Exceptional (5,647 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $1,058
    $667
    per traveler
    found 1 day ago
    Hotel Riu Plaza Chicago
  • Jan 13 - Jan 17

    Hotel Saint Clair- Magnificent Mile + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    8.6/10 - Excellent (2,373 reviews)
    "Receptionist was polite, professional, and efficient. Staff was polite and friendly. Location is quite convenient. In the heart of Chicago. Price was reasonable."
    Reviewed November 5, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $565
    $370
    per traveler
    found 1 day ago
    Hotel Saint Clair- Magnificent Mile
  • Jan 5 - Jan 10

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.2/10 - Wonderful (602 reviews)
    "If you are looking to stay in a condo type setting, this may be your spot. I checked in which you need to go through a process that takes 15 minutes, (do it before) and they automatically add a $25 per night fee for their gym and roof top. This was NOT published on Hotels.com or any other site. A total rip off as this is not a spa. There was no housekeeping. Checking in took 15 minutes in which there was little to no Wifi, so I had to go do this outside (crazy?). Do the check-in before..."
    Reviewed November 4, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $694
    $468
    per traveler
    found 1 day ago
    Level Chicago Fulton Market

Boulder Hill Hotel Deals

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.

Frequently Asked Questions

How much does a Boulder Hill vacation package cost?

Offering excellent value package deals from $318 on Expedia, you'll be pleasantly surprised at how much a vacation to Boulder Hill costs! Our packages make travel planning easier and save you more.

What are the cheapest months to go to Boulder Hill?

December, January and February are great times to search for cheap Boulder Hill vacation packages. Opting to travel in quieter months means you can generally find better prices on hotels and flights.

How many days is enough for Boulder Hill?

Generally, a handful of days is enough to go to the major attractions during your Boulder Hill vacation. But if you want to have some time to chill out or take day trips, consider extending your trip.

How to find the best Boulder Hill package deals?

Start your search for a Boulder Hill package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply some filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Boulder Hill package deal right away, just switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Boulder Hill adventure underway.

Is it cheaper to book a Boulder Hill vacation as a package?

Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll generally land a better deal than booking each component individually. And you'll still enjoy the freedom to create a tailored Boulder Hill vacation by choosing your favorite accommodation type, airline and car class.

When to book a vacation package to Boulder Hill?

If you're planning a spur-of-the-moment Boulder Hill trip, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can score awesome deals on your hotels and flights by booking ahead.

Does Expedia offer Book Now, Pay Later Boulder Hill vacation packages?

Your Boulder Hill break is meant to be an escape from your daily routine, not a source of money worries. So to allow you more flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.