Hillside Vacations from $348
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Your Hillside Vacation
An easy way to experience this vibrant city is with a custom-made Hillside vacation package. Base yourself in the neighborhood of Wicker Park, which is great for nightlife, bars and pubs and cafes or go someplace else — our packages are all about you. Any trip to Hillside needs a well-planned itinerary. Fill yours with major attractions such as Brookfield Zoo, Oakbrook Center Mall and Yorktown Shopping Center. Expedia can help you escape the everyday. Tailor your vacation to Hillside to suit your style of travel, whatever that may be.
The Latest Hillside vacation packages
Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Naperville/Warrenville
Save 100% on your flight
Price was $554, price is now $348 per person
$348
per person
Sep 23 - Sep 28
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,001 reviews)
Clean, quiet, decent food, friendly staff and nice rooms. Close to several places to eat and local entertainment. Not sure what else anyone would expect from a hotel.
Reviewed on Jul 6, 2026
Residence Inn by Marriott Chicago Bloomingdale
Save 100% on your flight
Price was $764, price is now $476 per person
$476
per person
Sep 23 - Sep 28
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (383 reviews)
Staff was welcoming. Continental breakfast was above average. We stayed in a 2bdr/2ba suite and just had a couple of minor annoyances with the room. The shower head was seemingly broken and there was cardboard folded and wedged in so that it would stay on the rod. If you touched it at all, it'd just fall off. The sink sprayer also did not stay up at the base of the faucet - it just dangled there in the sink. It made it a slight pain to do dishes. Neither problem was the end of the world, but attention to detail and the little things can be impacted.
Upon checking in (stayed Wed-Mon), we had asked for room cleanings (towels, bedding, and trash) for Friday and Sunday. They only did that Friday. We had to call the front desk for towels ourselves after getting back to the room from a full day of being in 100 degree weather and sweating to find we had no clean laundry.
Again, not the end of the world but it caused disappointment after having a much better experience there the year prior.
Reviewed on Jul 7, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $763, price is now $489 per person
$489
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,809 reviews)
Staff was very friendly and helpful. Room was clean. Free coffee and fruit in the AM.
Reviewed on Jul 9, 2026
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
Price was $1,078, price is now $707 per person
$707
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Amazing and beautiful hotel with caring and helpful staff!
Reviewed on Jul 8, 2026
What to do in Hillside
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
Hillside Hotel Deals
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$154 nightly
The price is $183 total per night from Jul 27 to Jul 28
$183 total
Jul 27 - Jul 28
Total with taxes and fees
8.2/10 Very Good! (1,727 reviews)
"Great place in a great location. Restaurant and breakfast buffet were excellent."
Reviewed on Jul 10, 2026
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$235 nightly
The price is $280 total per night from Aug 9 to Aug 10
$280 total
Aug 9 - Aug 10
Total with taxes and fees
9.2/10 Wonderful! (1,895 reviews)
"Unfortunately I didn't have the best experience. I am giving them an okay review because they did attempt to make it right. Without the check out employee in the morning; i probably would have gave this a very poor experience. He did take off the resort fee of $35ish & my $18 breakfast. When I arrived; ..."
Reviewed on Jul 10, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$210 nightly
The price is $250 total per night from Aug 10 to Aug 11
$250 total
Aug 10 - Aug 11
Total with taxes and fees
8/10 Very Good! (10,218 reviews)
"Our stay was great, best was comfortable and room was clean."
Reviewed on Jul 9, 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.
Find the Best Hillside Vacation Packages
Hillside Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
Population | 8,200 |
Max Temp Winter | 30ºF |
Max Temp Summer | 80ºF |
Top Sights | Brookfield Zoo, Rosemont Theatre and Parkway Bank Park Entertainment District |
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
