Oglesby Holidays from £473

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Your Oglesby Holiday

There's no better way to embark on an adventure than with one of our holiday packages to Oglesby. The small-town feel and friendly locals are a couple of the countless reasons you'll want to visit this fascinating city. Make your trip to Oglesby even more fulfilling by including some sightseeing. Starved Rock State Park, Grand Bear Falls Indoor Water Park and Matthiessen State Park are among the leading attractions you'll want to explore. Stop dreaming and start adventuring. Check out the many options on Expedia today and finally put your Oglesby holiday plans into gear!

Top Oglesby Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £711, price is now £473 per person
£473
per person
3 Oct - 7 Oct
found 1 day ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,825 reviews)
Staying here was nothing short of amazing thanks to this staff. They were very friendly, courteous and nice. Everyone was attentive and you can tell. They really loved working there and delivering service.

Reviewed on 20 Aug 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,928, price is now £1,124 per person
£1,124
per person
25 Oct - 1 Nov
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,159 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on 22 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 £1,488, price is now £956 per person
£956
per person
13 Nov - 17 Nov
found 22 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,670, price is now £1,090 per person
£1,090
per person
25 Oct - 1 Nov
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (666 reviews)
Hotel is located very centric. Nice view very quiet

Reviewed on 22 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 £2,097, price is now £1,394 per person
£1,394
per person
25 Oct - 1 Nov
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,087 reviews)
Staff was amazing!! Everything was so easy checking in and checking out. The stay was great! It was so nice having the pier to ourselves after hours.

Reviewed on 20 Aug 2025

Oglesby Essential Information

Language
English
Currency
U.S dollars
Population
3,600
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Starved Rock State Park, Matthiessen State Park and Grand Bear Falls Indoor Water Park

Top hotels in Oglesby

Days Inn by Wyndham Oglesby/ Starved Rock

Days Inn by Wyndham Oglesby/ Starved Rock

2 out of 5
120 N Lewis Ave, Oglesby, IL
Fully refundableReserve now, pay when you stay
The price is £69 per night from 24 Aug to 25 Aug
£69
24 Aug - 25 Aug
includes taxes & fees
8/10 Very Good! (1,001 reviews)
"Easy to check-in and reasonable fee for our dog. Staff quickly responded to our request for extra pillows because of our back issues."

Reviewed on 21 Aug 2025

Days Inn by Wyndham Oglesby/ Starved Rock
Best Western Oglesby Inn

Best Western Oglesby Inn

2.5 out of 5
900 Holiday Street, Oglesby, IL
Fully refundableReserve now, pay when you stay
The price is £89 per night from 24 Aug to 25 Aug
£89
24 Aug - 25 Aug
includes taxes & fees
8/10 Very Good! (1,000 reviews)
"Clean and convenient."

Reviewed on 19 Aug 2025

Best Western Oglesby Inn
Starved rock area country ranch

Starved rock area country ranch

Oglesby, IL
The price is £195 per night from 24 Aug to 25 Aug
£195
24 Aug - 25 Aug
includes taxes & fees
9.2/10 Wonderful! (20 reviews)
"Very clean and had everything we needed, fresh towels."

Reviewed on 11 Jul 2025

Starved rock area country ranch
See all 358 properties in Oglesby
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Popular places to visit

Dickinson House

Enjoy an outing to Dickinson House during your stay in Oglesby. Wander around the parks in this family-friendly area or simply enjoy its restaurants.

Dickinson House

What to do in Oglesby

Tandem Guided Kayak Tour Near Chicago

Tandem Guided Kayak Tour Near Chicago

£44
per adult
Tandem Guided Kayak Tour Near Chicago
Single Guided Kayaking Tour near Chicago

Single Guided Kayaking Tour near Chicago

£65
per adult
100% of travellers recommend
Single Guided Kayaking Tour near Chicago
See all activities in Oglesby

Frequently asked questions

How much does an Oglesby travel package cost?
Get your credit card ready, because a trip to Oglesby starts from just £473. When you bundle your hotels, flights and car rentals into a travel package, you'll score the best deals.
If I'm not able to travel, can I cancel my Oglesby travel package?
You can cancel your Oglesby booking if your travel plans have been upended. Whether you'll incur a penalty or not depends on your airline, hotel or car rental company. You may be able to cancel or change for free if you booked in the last 24 hours. Head to our Customer Service Portal to learn more.
How do I get a cheap travel package to Oglesby?
Bundle your hotels and flights, add extras such as a rental car or activities, and save with an Oglesby travel package. You won't just score amazing discounts on your adventure — you'll have loads of choice at your fingertips too. When you book with Expedia, you can select from more than 550 airlines and 1,000,000 properties around the globe. Your unforgettable holiday begins right here, right now!
Does Expedia offer Book Now, Pay Later Oglesby holidays?
We sure do. Expedia has teamed up with online lender Klarna to help you conveniently pay for your trip in manageable instalments. Simply pick the payment plan best suited to your needs during checkout and take away the stress of budgeting for your trip. Be sure to bundle your flights, accommodation and activities with Expedia to get the biggest bang for your buck. Check out our flexible payment options below:

  • Pay monthly holidays: Klarna has convenient monthly payment plans that suit all budgets, so you can lock in that well-deserved holiday sooner.
  • Pay in instalments holidays: If you'd like to pay off your getaway in multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: Clicking the "book now" button is much easier with this payment plan. Put down a small deposit on your booking and then get on your way.

Where should I stay in Oglesby?
Close to the action. Many visitors favor hotels in the vicinity of popular sights, such as Matthiessen State Park, Deer Park Country Club and Lock 16 Visitor Centre & LaSalle Canal Boat.
What are the top hotels in Oglesby?
Get your trip off to a good start by booking a stay at Hyatt Regency Chicago. It's one of most sought-after hotels in Oglesby. Another cosy option is The Godfrey Hotel Chicago.
How far in advance should I book my Oglesby holiday?
Reserving your spot early with Expedia means one less thing to have to worry about. Most carriers advertise prices up to a year in advance. This is generally the cheapest time to book. If circumstances have left you booking late, low prices to Oglesby sometimes occur a few weeks before departure.
What does an Expedia Oglesby travel package include?
It comes down to what you're looking for. If you're travelling by yourself, you might decide to bundle hotels and flights. Taking the whole crew to Oglesby? A travel package that includes hotels, rental cars and flights might be a better fit. Expedia gives you the freedom to customize your travel package.
What should I know before booking an Oglesby travel package?
When you book your flights, hotels and car rentals together, you'll be rewarded with terrific discounts. Whether you're organising a rural escape in a cottage or would rather stay in a comfortable hotel in the city, Expedia can help make it happen.
Can I choose my airline with an Oglesby Expedia travel package?
With a travel package, you're the one in charge. Whether you'd prefer to fly to Oglesby in economy or first class, simply choose from the available airline options. Expedia has access to over 550 airline partners worldwide.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.