Rolling Meadows Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Rolling Meadows Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
27 Sept - 29 Sept
found 12 hours ago
Return flight included
New York (LGA) to Chicago (ORD)
8.2/10 Very Good! (1,842 reviews)
No refrgerator, can hear the noise coming from the street. Room us clean and smell good

Reviewed on 14 Jul, 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
27 Sept - 29 Sept
found 12 hours ago
Return flight included
New York (LGA) to Chicago (ORD)
9.2/10 Wonderful! (1,769 reviews)
The location is great, with a fantastic staff and an easy check-in process. I can walk to almost everything, and the bus station is right next to the door.

Reviewed on 16 Jul, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
27 Sept - 29 Sept
found 12 hours ago
Return flight included
New York (LGA) to Chicago (ORD)
9.4/10 Exceptional! (2,053 reviews)
Great location, but the $50.00 early check-in fee is ridiculous. Also, the comforter on the bed has seen better days.

Reviewed on 15 Jul, 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
27 Sept - 29 Sept
found 12 hours ago
Return flight included
New York (LGA) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
I loved the location of the property, and the overall concept of something fun and funky, but I had a "higher end" room, and it was right near the elevator, so I got a lot of noise on that side, plus the El from the other side. The rug wasn't super clean (although the bedding and the rest of the room were a delight). The most annoying thing was the TV. Anything I turned it to, 10 minutes later to the minute, it went back to the Virgin channel #1, here are all our hotels in the world. I really hated having to stay on top of a show, when usually I want the tv on as background while I'm getting ready, etc. Also, this hotel's amenities were oversold, i.e., good luck getting on the rooftop, especially if you just wanted a quiet sip of a drink. I loved the cafe and the staff, though, everyone was very pleasant.

Reviewed on 15 Jul, 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Downtown Chicago
per person
27 Sept - 29 Sept
found 12 hours ago
Return flight included
New York (LGA) to Chicago (ORD)
8.4/10 Very Good! (3,506 reviews)
Clean and the suites are room

Reviewed on 16 Jul, 2025

Top hotels in Rolling Meadows

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave, Rosemont, IL
Fully refundableReserve now, pay when you stay
The price is S$243 per night from 14 Aug to 15 Aug
S$243
14 Aug - 15 Aug
includes taxes & fees
8.6/10 Excellent! (1,731 reviews)
"Not sure why this hotel is a 3.7 but it was great . Very clean . Polite staff . Hot showers"

Reviewed on 14 Jul, 2025

Hyatt Regency O'Hare Chicago
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$270 per night from 8 Aug to 9 Aug
S$270
8 Aug - 9 Aug
includes taxes & fees
8/10 Very Good! (2,084 reviews)
"Great location for quick access to ORD travel. Rather pricey. Room was nice except way too cold on arrival (about 60 deg per thermostat) and couldn't get the temp to increase by setting thermostat higher."

Reviewed on 15 Jul, 2025

Hilton Chicago O'Hare Airport
Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$257 per night from 8 Aug to 9 Aug
S$257
8 Aug - 9 Aug
includes taxes & fees
8.4/10 Very Good! (1,083 reviews)
"For the price we paid, i was disappointed to find that our room smelt like cigarettes. A few fixtures in the room seem to be stained from smoke and the carpet didn’t feel clean. But aside from that, the pool was clean, bathroom was nice, breakfast was expensive but it was okay. Stayed for two days. ..."

Reviewed on 11 Jul, 2025

Marriott Chicago O'Hare
See all 2,251 properties in Rolling Meadows
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.

Popular places to visit

Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

4.5/5(40 reviews)

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
McCormick Place

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Millennium Park which includes modern architecture, a city and autumn leaves

Millennium Park

4.5/5(147 reviews)

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park

What to do in Rolling Meadows

River tour boat in Chicago

Architecture River Tour

S$53
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

S$52
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

S$58
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Rolling Meadows

Frequently asked questions

How much does a Rolling Meadows holiday package cost?
Offering great value package deals from S$437 on Expedia, you'll be pleasantly surprised at how much a holiday to Rolling Meadows costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Rolling Meadows?
You can usually find lower rates and better availability in December, January and February. Browse our cheap Rolling Meadows holiday packages and you could land some excellent off-season deals.
How many days is enough for Rolling Meadows?
Generally, a handful of days is enough to explore the main sights during your Rolling Meadows holiday. But if you prefer to have some time to rest or take day tours, consider extending your trip.
How to find the best Rolling Meadows package deals?
Landing a cheap Rolling Meadows package deal is a breeze with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your budget range, add some filters and see what's available. You can tweak your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Sort the results by "Price: low to high" to discover the most affordable Rolling Meadows package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Rolling Meadows holiday as a package?
An Expedia holiday package could land you considerable savings when compared to arranging flights and stays separately. Better still, you can tailor your Rolling Meadows getaway to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a holiday package to Rolling Meadows?
Secure incredible discounts by reserving your flights in advance with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for an impromptu Rolling Meadows adventure.
How to plan a trip to Rolling Meadows?

  1. Choose when to go: Check your schedule and pack your bags. Your preferred season and the type of activities on offer will also help you decide when to escape to Rolling Meadows.
  2. Budget wisely: In addition to the price of your hotel, you'll need to factor in other expenses too. These include transportation, flights and food. Also, set aside some extra funds for unexpected expenses that could crop up during your trip to Rolling Meadows.
  3. Determine how many days away: Start by making a list of all the attractions and activities you'd like to experience in Rolling Meadows. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to pick a Rolling Meadows 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.