Hillcrest Trip

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Top Hillcrest Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
16 Aug - 21 Aug
found 1 day ago
Return flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,781 reviews)
Great location and wonderful staff

Reviewed on 1 Jul 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
16 Aug - 21 Aug
found 1 day ago
Return flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,623 reviews)
Amazing hotel with large rooms right off Michigan avenue. Staff is amazing, they are always friendly and helpful.

Reviewed on 27 Jun 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
16 Aug - 21 Aug
found 1 day ago
Return flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Staff was very friendly and helpful. We had a great stay in every way possible!

Reviewed on 30 Jun 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
16 Aug - 21 Aug
found 1 day ago
Return flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,796 reviews)
The staff hospitality was incredible 💖

Reviewed on 2 Jul 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
16 Aug - 21 Aug
found 1 day ago
Return flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,769 reviews)
Comfortable, stylish, friendly hotel in a fabulous location near Millennium Park, Art Institute, and Riverwalk. Friendly staff throughout but the cherry on top was Antoine who checked our bags and arranged out transportation to the airport when we checked out

Reviewed on 29 Jun 2025

Top hotels in Hillcrest

Country Inn & Suites by Radisson, Sycamore, IL
Country Inn & Suites by Radisson, Sycamore, IL
2.5 out of 5
1450 South Peace Road, Sycamore, IL
Fully refundable
The price is ₹7,285 per night from 27 Jul to 28 Jul
₹7,285
₹8,085 total
27 Jul - 28 Jul
includes taxes & fees
8.6/10 Excellent! (828 reviews)
Nice.
"Enjoyed the stay. Elevator was out so booked me to the 2nd floor. Enjoyed."

Reviewed on 30 Jun 2025

Country Inn & Suites by Radisson, Sycamore, IL
Hampton Inn DeKalb, IL
Hampton Inn DeKalb, IL
3 out of 5
663 S. Annie Glidden Road, DeKalb, IL
Fully refundableReserve now, pay when you stay
The price is ₹10,126 per night from 13 Jul to 14 Jul
₹10,126
₹11,492 total
13 Jul - 14 Jul
includes taxes & fees
9.2/10 Wonderful! (918 reviews)
"Professional and friendly staff. Cleanliness of hotel"

Reviewed on 30 Jun 2025

Hampton Inn DeKalb, IL
Best Western Sycamore Inn
Best Western Sycamore Inn
2.5 out of 5
1935 Dekalb Ave, Sycamore, IL
Fully refundableReserve now, pay when you stay
The price is ₹7,811 per night from 10 Jul to 11 Jul
₹7,811
₹8,669 total
10 Jul - 11 Jul
includes taxes & fees
8/10 Very Good! (330 reviews)
"The shower is nice and housekeeping came most days. However the breakfast is awful. Packets of oatmeal, now a yogurt machine. Hot water dispenser never properly cooks the oatmeal. For these they provide "mix ins" which included dried apples amd brown sugar. That's it. The hot opetions always involve ..."

Reviewed on 28 Jun 2025

Best Western Sycamore Inn
See all 61 properties in Hillcrest
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 Hillcrest holiday package cost?
Offering great value package deals from ₹47,490 on Expedia, you'll be pleasantly surprised at how much a holiday to Hillcrest costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Hillcrest?
If you'd like to book a cheap Hillcrest holiday package, consider travelling in January, February and November. You'll usually find lower rates on flights and accommodation during these months --- perfect for travellers wishing to save money.
How many days is enough for Hillcrest?
With a well-planned itinerary, you can easily tick off the top Hillcrest sights in a few days. But if you want to discover hidden spots or go on day trips, think about booking your Hillcrest holiday for longer.
How to find the best Hillcrest package deals?
Begin your search for a Hillcrest package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Popular locations" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the ideal Hillcrest package deal right away, just tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Hillcrest getaway off to a flying start.
Is it cheaper to book a Hillcrest holiday as a package?
Expedia holiday packages are designed to give you more bang for your buck. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component individually. And you'll still get the flexibility to create a tailored Hillcrest holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Hillcrest?
If you've got your Hillcrest holiday dates finalized, book as early as you can to score some fantastic deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Hillcrest?

  1. Choose your dates: The things you plan to do in Hillcrest and your favourite season can help you decide when to travel.
  2. Budget wisely: On top of the price of your stay, you should consider other expenses too. These include transportation, food and flights. Also, put aside some extra funds for unexpected expenses that could arise during your trip to Hillcrest.
  3. Work out your trip length: Consider how long you'd like to spend discovering Hillcrest. Plan your itinerary so you can get to all the attractions and experiences you're interested in without rushing.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to choose a Hillcrest 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.