Oglesby Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

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 Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,389, price is now CA $921 per person
CA $921
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
Excellent spot, in the perfect location. Parking at the property is pretty expensive, but there are cheaper parking garages close by.

Reviewed on Jul 6, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Price was CA $3,926, price is now CA $2,363 per person
CA $2,363
per person
Sep 20 - Sep 23
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
We came to the property for my wife’s 40th birthday celebration. From the moment we walked in through the doors, we felt pampered. Everyone on staff was friendly, high energy, and always willing to help. The housekeeping staff was top notch as they went above and beyond with expectation on not only keeping things clean, but organizing our clutter, leaving thoughtful birthday treats, and making us feel comfortable. I now do not want to travel without staying at a 4 seasons property. They made our experience 10 times better!

Reviewed on Jul 6, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,047, price is now CA $1,235 per person
CA $1,235
per person
Sep 24 - Sep 28
found 15 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
We had a great stay at Level. I think it’s a really good option for a longer trip, especially if you want more of an apartment-style setup and a convenient location. The staff was amazing from start to finish and truly made the stay stand out. Everyone was kind, helpful, and welcoming, and the service alone would make me come back. The location is also very convenient and worked well for getting around Chicago, especially if you don’t mind doing a bit of walking. For our family, I think it felt a little more geared toward professionals or longer stays than a traditional family hotel, but overall we had a very positive experience. If you’re staying in Chicago for more than a couple of nights and want something comfortable and convenient, I would definitely recommend it.

Reviewed on Jul 2, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was CA $2,110, price is now CA $1,436 per person
CA $1,436
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
Convenient location and friendly staff.

Reviewed on Jul 7, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $2,153, price is now CA $1,484 per person
CA $1,484
per person
Sep 20 - Sep 23
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,136 reviews)
Great location can get a bit noisy but really nice hotel.

Reviewed on Jul 8, 2026

Ready to book your vacation to Oglesby?

 

Choose your dates

Oglesby Hotel Deals

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 $127 per night from Jul 16 to Jul 17
CA $127
CA $140 total
Jul 16 - Jul 17
includes taxes & fees
8.2/10 Very good! (1,006 reviews)
"It's a good location for people wanting to hike at Starved Rock."

Reviewed on Jul 6, 2026

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 CA $155 per night from Jul 12 to Jul 13
CA $155
CA $172 total
Jul 12 - Jul 13
includes taxes & fees
8.2/10 Very good! (1,004 reviews)
"Nos quedamos por la alberca pero la agua fría y al entrar olía a cigarro y el cuarto a humedad Si está limpio y el desayuno está bien por el precio está bien"

Reviewed on Jul 5, 2026

Best Western Oglesby Inn
Starved rock area country ranch

Starved rock area country ranch

Oglesby IL
The price is CA $230 per night from Jul 10 to Jul 11
CA $230
CA $364 total
Jul 10 - Jul 11
includes taxes & fees
9.2/10 Wonderful! (28 reviews)
"The property was good, but the oven didn’t work and the water smelled. And then the host messaged me many days later to accuse me of breaking a stove that we didn’t even touch. I am refusing to pay for something that I did not break, even touch, or really can’t even tell you what the stove looked ..."

Reviewed on Jun 25, 2026

Starved rock area country ranch
See all 360 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

Stay near popular Oglesby attractions

Matthiessen State Park

9.4/10 (216 reviews)
Look down the chute of Cascade Falls from a rickety bridge and admire the brilliant hues decorating the canyon’s sandstone walls in this eclectic park.
See properties

Frequently asked questions

How much does an Oglesby vacation package cost?
You'll find cheap prices from CA $921 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.