Eola Holidays

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Eola Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was S$3,839, price is now S$2,719 per person
S$2,719
per person
9 Oct - 15 Oct
found 16 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
8.8/10 Excellent! (1,925 reviews)
Check in and out was seamless! Got excellent help with bags and access to amenities! Great location it was about a 9 min walk to Riverwalk, Hop on Bus; felt safe and area was clean

Reviewed on 18 Aug, 2025

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$4,369, price is now S$2,983 per person
S$2,983
per person
9 Oct - 15 Oct
found 16 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (1,007 reviews)
Loved the hotel. Very clean and comfortable. The gentleman who checked us out was not the most friendly, but everyone else was super helpful!

Reviewed on 18 Aug, 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
Price was S$4,258, price is now S$2,932 per person
S$2,932
per person
9 Oct - 15 Oct
found 16 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (2,063 reviews)
My family and I love this place

Reviewed on 19 Aug, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$5,300, price is now S$3,680 per person
S$3,680
per person
9 Oct - 15 Oct
found 16 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug, 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was S$3,827, price is now S$2,741 per person
S$2,741
per person
9 Oct - 15 Oct
found 16 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
8.2/10 Very Good! (1,991 reviews)
Terrible mattresses, old and crunchy or something; bad lumpy pillows. No coffee or water in the room. If you want free coffee, you gotta track to the lobby during coffee hours and pay a "resort" fee for the experience.

Reviewed on 17 Aug, 2025

Top hotels in Eola

DoubleTree by Hilton Lisle Naperville

DoubleTree by Hilton Lisle Naperville

4 out of 5
3003 Corporate West Dr, Naperville, IL
Fully refundableReserve now, pay when you stay
The price is S$119 per night from 7 Sept to 8 Sept
S$119
7 Sept - 8 Sept
includes taxes & fees
7.8/10 Good! (1,085 reviews)
"It was great and clean"

Reviewed on 17 Aug, 2025

DoubleTree by Hilton Lisle Naperville
SureStay Plus Hotel by Best Western Chicago Lombard

SureStay Plus Hotel by Best Western Chicago Lombard

2.5 out of 5
222 E 22nd Street, Lombard, IL
The price is S$102 per night from 16 Sept to 17 Sept
S$102
16 Sept - 17 Sept
includes taxes & fees
8.8/10 Excellent! (2,189 reviews)
"The rooms were nice if a bit dated. Everything was clean and we had a fantastic stay. Special thanks to Patrick at the front desk for leaving a great lasting impression. Super helpful and friendly staff! Would highly recommend."

Reviewed on 18 Aug, 2025

SureStay Plus Hotel by Best Western Chicago Lombard
Chicago Club Inn & Suites

Chicago Club Inn & Suites

3 out of 5
630 Pasquinelli Dr, Westmont, IL
Fully refundableReserve now, pay when you stay
The price is S$109 per night from 17 Sept to 18 Sept
S$109
17 Sept - 18 Sept
includes taxes & fees
7/10 Good! (1,239 reviews)
"We have stayed here several times and it has been nice. The property needs maintenance such as regular grooming of the grass and shrubs."

Reviewed on 17 Aug, 2025

Chicago Club Inn & Suites
See all 754 properties in Eola
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 Eola

River tour boat in Chicago

Architecture River Tour

S$53
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

S$58
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
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 all activities in Eola

Frequently asked questions

How much does an Eola holiday package cost?
You can pick up a holiday package to this destination from S$2,719 on Expedia. But how much your holiday to Eola costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Eola?
If you'd like to score a cheap Eola holiday package, consider visiting in January, February and November. You're likely to find lower prices on airfares and hotels during these quieter months — ideal for a budget-friendly break.
How many days is enough for Eola?
Typically, a handful of days is enough to explore the major attractions during your Eola holiday. But if you want to have time to unwind or go on day tours, consider extending your trip.
How to find the best Eola package deals?
Use Expedia's filter tool to find some fabulous Eola package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Eola package deals in the off-peak season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your holiday package well in advance.
Is it cheaper to book an Eola holiday as a package?
Expedia holiday packages are designed to make your money go further. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll generally get a better deal than booking each component individually. And you'll still have the flexibility to create a tailored Eola holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Eola?
If you're considering a spur-of-the-moment Eola holiday, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land awesome deals on your hotels and flights by booking well in advance.
How to plan a trip to Eola?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to go to Eola.
  2. Figure out your budget: Ensure you have enough money to pay for everything from transportation and meals to activities and flights. Your hotel will likely be the biggest expense during your trip to Eola.
  3. Decide how long to go away for: Now that you're up to speed on Eola, you can work out the ideal length of your break. Create a draft plan and give yourself enough time to get through everything on your must-do list.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to find an Eola 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.