Deals on vacations and trips to Winnebago County

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Rockford featuring a city and general coastal views

Rockford

Vacations
Rockford
I took this of my Twin sister. I love how the frozen lake looks at this time of day.

Loves Park

Vacations
Loves Park

Winnebago County flight + hotel vacation packages

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

The Royal Sonesta Chicago Downtown

4 out of 5
Downtown Chicago
Price was $403, price is now $273 per person
$273
per person
Jan 30 - Feb 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, conference space, and valet parking. WiFi in public areas, luggage storage, and concierge services are also on offer.
Illinois Beach Hotel

Illinois Beach Hotel

2 out of 5
Save 100% on your flight
Price was $450, price is now $295 per person
$295
per person
Feb 13 - Feb 18
found 13 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area is provided and the front desk is staffed around-the-clock.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $983, price is now $667 per person
$667
per person
Jan 30 - Feb 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,660, price is now $1,138 per person
$1,138
per person
Feb 18 - Feb 24
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $622, price is now $432 per person
$432
per person
Feb 19 - Feb 23
found 10 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
A 24-hour gym, valet parking, and concierge services are featured at this hotel. WiFi in public areas is free. A coffee shop, express check-out, and luggage storage are also on offer.

Top Winnebago County hotels deals

Baymont by Wyndham Rockford

Baymont by Wyndham Rockford

3 out of 5
662 N Lyford Rd Rockford IL
Free Cancellation
Reserve now, pay when you stay
$66 nightly
The price is $76 total per night
$76 total
Jan 18 - Jan 19, 2026
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.
Pool
Breakfast included
Holiday Inn Rockford by IHG

Holiday Inn Rockford by IHG

3 out of 5
7550 E State Street Rockford IL
Free Cancellation
$82 nightly
The price is $93 total per night
$93 total
Dec 28 - Dec 29
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the gym and perks like a free area shuttle.
Pool
Free airport shuttle
Embassy Suites by Hilton Rockford Riverfront

Embassy Suites by Hilton Rockford Riverfront

3.5 out of 5
416 S Main Street Rockford IL
Free Cancellation
Reserve now, pay when you stay
$130 nightly
The price is $149 total per night
$149 total
Dec 29 - Dec 30
Total with taxes and fees
This hotel features 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Unwind with a drink at one of the 2 bars/lounges and enjoy the free buffet breakfast each morning.
Pool
Breakfast included
Home2 Suites by Hilton Loves Park Rockford

Home2 Suites by Hilton Loves Park Rockford

3 out of 5
4150 N Bell School Road Loves Park IL
Free Cancellation
Reserve now, pay when you stay
$89 nightly
The price is $101 total per night
$101 total
Jan 18 - Jan 19, 2026
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Hilton Garden Inn Rockford

Hilton Garden Inn Rockford

3 out of 5
7675 Walton St Rockford IL
Free Cancellation
Reserve now, pay when you stay
$107 nightly
The price is $122 total per night
$122 total
Dec 28 - Dec 29
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free parking, a snack bar/deli, and a lobby fireplace are also offered.
Pool
Pet friendly
La Quinta Inn & Suites by Wyndham Rockford

La Quinta Inn & Suites by Wyndham Rockford

3 out of 5
7401 Walton St Rockford IL
Free Cancellation
Reserve now, pay when you stay
$71 nightly
The price is $80 total per night
$80 total
Dec 23 - Dec 24
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.
Pool
Breakfast included
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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.

Photos of local treasures

Browse Winnebago County vacation photos for more inspiration

Photo provided by Rockford Area Convention & Visitors Bureau
Photo provided by Rockford Area Convention & Visitors Bureau
Photo provided by Rockford Area Convention & Visitors Bureau
Photo provided by Rockford Area Convention & Visitors Bureau
Photo provided by Rockford Area Convention & Visitors Bureau
Photo provided by Rockford Area Convention & Visitors Bureau
Photo provided by Rockford Area Convention & Visitors Bureau
Photo provided by Rockford Area Convention & Visitors Bureau
Photo provided by Rockford Area Convention & Visitors Bureau
Photo provided by Rockford Area Convention & Visitors Bureau

Frequently asked questions

How much are vacation packages to Winnebago County?
With vacation packages on offer for just $273, you won't need to drain your bank balance to travel to Winnebago County. Travelocity is here to help. Bundle your experiences, flights and hotels into a package and receive some exciting discounts. The more you book, the more you save.
Where can I get the best vacation package deals for Winnebago County?
It's hard to look past Travelocity when it comes to crafting your Winnebago County package deal. There are as many as 400 partner airlines and 1,000,000 properties worldwide to select from. Reserve your trip now and get ready to tick another exciting destination off your must-see list.
Why should I purchase my Winnebago County vacation bundle via Travelocity?
With first-rate service, 24/7 customer support and some of the most gorgeous escapes on offer, you'll never roam alone. And if you find a lower price, we'll match it. That's our Price Match Guarantee.
Can I save on my Winnebago County car rental if I book it with hotels and flights?
You sure can with our Winnebago County vacation packages. With one of these, there are loads of ways to stretch your travel budget further. Bundle any two or more car, flight, hotel and tour bookings and see the savings start to pile up. With a rental car, all the key sights in and around Winnebago County are a fun road trip away.
Which airport is best for Winnebago County?
Winnebago County has two main hubs — Dane County Regional Airport (MSN) and Rockford, IL (RFD-Greater Rockford).
What is there to do in Winnebago County?
Winnebago County has hidden gems at every corner, however make sure you plan a visit to both Anderson Japanese Gardens and BMO Harris Bank Center during your stay. These landmarks shouldn't be missed.

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