Oglesby Vacation Packages

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Your Oglesby Vacation

There's no better way to embark on an adventure than with one of our vacation 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 vacation plans into gear!

Top Oglesby Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Oct 11 - Oct 15
found 14 hours ago
Roundtrip flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
Will go back again for next Chicago trip

Reviewed on Jul. 21, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
THE CARPET IS VERY DIRTY.

Reviewed on Jul. 21, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Oct 11 - Oct 15
found 17 hours ago
Roundtrip flight included
Edmonton (YEG) to Chicago (ORD)
9/10 Wonderful! (324 reviews)
Nice rooms and amenities, we would stay here again. This was a nice place! We love the location and the fact it was dog friendly. Lots to do for eats/drinks in walking distance and they have a lovely dog area adjacent to the pool on the 8th floor. Nice not to have to go down to the street for potty breaks. Taking off a star for the simple fact that they only have feather pillows (so I had to buy my own hypoallergenic one) and their parking lot was full so we had to park a few blocks away.

Reviewed on Jul. 19, 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9/10 Wonderful! (639 reviews)
The property in itself was not terrible, but I expected better.

Reviewed on Jul. 19, 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (3,357 reviews)
Beautiful location, very professional staff

Reviewed on Jul. 21, 2025

Ready to book your vacation to Oglesby?

 

Choose your dates

Oglesby Hotel Deals

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 CA $150 per night from Jul 22 to Jul 23
CA $150
CA $166 total
Jul 22 - Jul 23
includes taxes & fees
8/10 Very Good! (1,003 reviews)
"Clean Quite Good Location Plenty of Parking Parked Pickup with Camper & Motorcycle with no issues"

Reviewed on Jul. 14, 2025

Best Western Oglesby Inn
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 CA $106 per night from Aug 3 to Aug 4
CA $106
CA $118 total
Aug 3 - Aug 4
includes taxes & fees
8/10 Very Good! (1,001 reviews)
"Staff were helpful and responsive to needs. I believe the hotel is being upgraded; it appeared new carpet was being installed. Some of the room flooring and fixtures were older. It was suitable for one night as we were passing through!"

Reviewed on Jun. 29, 2025

Days Inn by Wyndham Oglesby/ Starved Rock
Starved rock area country ranch

Starved rock area country ranch

Oglesby
The price is CA $222 per night from Jul 30 to Jul 31
CA $222
CA $341 total
Jul 30 - Jul 31
includes taxes & fees
9.2/10 Wonderful! (19 reviews)
Great reset from city life
"The stay was amazing! We enjoyed the close proximity of the state parks and the privacy we had."

Reviewed on Jun. 26, 2025

Starved rock area country ranch
See all 348 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 Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Discover the most popular places to visit in Oglesby

Deer Park Country Club

Enjoy a round of golf in Oglesby at Deer Park Country Club. Wander around the parks in this relaxing area, or simply enjoy its restaurants.

Deer Park Country Club

What to do in Oglesby

Tandem Guided Kayak Tour Near Chicago

Tandem Guided Kayak Tour Near Chicago

CA $121
per adult
Tandem Guided Kayak Tour Near Chicago
See all activities in Oglesby

Frequently asked questions

How much does an Oglesby vacation package cost?
You'll find cheap prices from CA $1,492 on Expedia for your Oglesby escape. However, factors like the hotel choice, length of stay and season will determine how much your vacation to Oglesby costs.
What are the cheapest months to go to Oglesby?
If you're looking to score a cheap Oglesby vacation package, consider visiting in December, January and February. You're likely to find better prices on accommodations and flights during these quieter months — perfect for budget-conscious travellers.
How many days is enough for Oglesby?
With a well-organized itinerary, you can easily hit the most popular Oglesby attractions in a few days. But if you prefer to explore off the beaten track or go on day trips, consider booking your Oglesby vacation for longer.
Is it worth booking a vacation package to Oglesby?
Oglesby offers everything you need for an unforgettable trip. Get your Oglesby vacation off to a flying start by exploring major attractions like Matthiessen State Park.
How to find the best Oglesby package deals?
Use Expedia's handy filters to find some of the best Oglesby package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Oglesby package deals in the off-season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book an Oglesby vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging stays and flights individually. Better still, you can personalize your Oglesby escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Oglesby?
If you've got your Oglesby vacation dates locked in, book early to bag some terrific deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for travelling on a whim.
How to plan a trip to Oglesby?

  1. Choose when to travel: Check your calendar and get your bags packed. Your favourite season and the available activities will also help you decide when to vacation in Oglesby.
  2. Set a budget: Factor in expenses like flights, food and transportation when calculating how much to save for your trip to Oglesby. Then, pick a hotel that matches your budget, whether that's an economical stay or a more upscale retreat.
  3. Decide how long to go away for: Now that you're up to speed on Oglesby, you can work out the ideal length of your vacation. Pull together a rough plan and allocate enough time to cover everything you want to do.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to pick an Oglesby vacation 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.