Search Deals on
Milton Vacation Packages

Build your package with 2 more options

Milton Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Studio 6 Pensacola, FL - West I-10

Studio 6 Pensacola, FL - West I-10

2.5 out of 5
Price was $593, price is now $478 per person
$478
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Pensacola (PNS)
Book a stay at this business-friendly hotel in Pensacola. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Five Flags Speedway and DeLuna Lanes Bowling Center are located nearby.

The Pensacola Beach Resort

The Pensacola Beach Resort

4 out of 5
Price was $967, price is now $711 per person
$711
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Pensacola (PNS)
Book a stay at this beach hotel in Pensacola Beach. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Pensacola Beach Boardwalk and Fort Pickens are located nearby.

Landing Furnished Apartments Pensacola near Coral Creek

Landing Furnished Apartments Pensacola near Coral Creek

3 out of 5
Price was $986, price is now $750 per person
$750
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Pensacola (PNS)
Stay at this apartment in Pensacola. Enjoy an outdoor pool, a fitness center, and an in-room coffeemaker. Popular attractions Pensacola Beach Beaches and Perdido Key Beach are located nearby.

Emerald Isle

Emerald Isle

3 out of 5
Price was $1,131, price is now $904 per person
$904
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Pensacola (PNS)
Book a stay at this beach condo in Pensacola Beach. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Pensacola Beach Boardwalk and Casino Beach are located nearby.

Motel 6 Pensacola, FL - NAS

Motel 6 Pensacola, FL - NAS

2.5 out of 5
Price was $621, price is now $498 per person
$498
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Pensacola (PNS)
Book a stay at this family-friendly motel in Pensacola. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Pensacola Beach Beaches and Warrington Village Shopping Center are located nearby.

Wavecrest Lodge

Wavecrest Lodge

2.5 out of 5
Price was $637, price is now $514 per person
$514
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
Book a stay at this beach hotel in Fort Walton Beach. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Okaloosa Island Beach and HarborWalk Village are located nearby.

Candlewood Suites Pensacola - University Area by IHG

Candlewood Suites Pensacola - University Area by IHG

2.5 out of 5
Price was $634, price is now $513 per person
$513
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Pensacola (PNS)
Book a stay at this business-friendly hotel in Pensacola. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions University Town Plaza and Grizzly Axes are located nearby.
Na

Reviewed on Sep 25, 2026

Landing Apartments - Northwest Pensacola

Landing Apartments - Northwest Pensacola

4 out of 5
Price was $825, price is now $668 per person
$668
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Pensacola (PNS)
Book a stay at this business-friendly apartment in Pensacola. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Five Flags Speedway and Perdido River Wildlife Management Area are located nearby.

Milton Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Motel 6 Pensacola, FL - NAS

Motel 6 Pensacola, FL - NAS

2.5 out of 5
Price was $525, price is now $426 per person
$426
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Pensacola (PNS)
The Pensacola Beach Resort

The Pensacola Beach Resort

4 out of 5
Villa Sabine
Price was $795, price is now $628 per person
$628
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Pensacola (PNS)
Wavecrest Lodge

Wavecrest Lodge

2.5 out of 5
Okaloosa Island
Price was $637, price is now $514 per person
$514
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
Sundrift Inn

Sundrift Inn

3 out of 5
Okaloosa Island
Price was $620, price is now $504 per person
$504
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)

Milton Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Pensacola Beach Resort

The Pensacola Beach Resort

4 out of 5
Villa Sabine
Price was $967, price is now $711 per person
$711
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Pensacola (PNS)
Landing Furnished Apartments Pensacola near Coral Creek

Landing Furnished Apartments Pensacola near Coral Creek

3 out of 5
Price was $986, price is now $750 per person
$750
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Pensacola (PNS)
The Island Resort at Fort Walton Beach

The Island Resort at Fort Walton Beach

4 out of 5
Okaloosa Island
Price was $1,051, price is now $816 per person
$816
per person
Nov 1 - Nov 8
found 3 hours ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
Emerald Isle

Emerald Isle

3 out of 5
Villa Primera
Price was $1,131, price is now $904 per person
$904
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Pensacola (PNS)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Mon, Oct 26 - Mon, Nov 2
ATL
Hartsfield-Jackson Atlanta Intl.
PNS
Pensacola Intl.
$150 Roundtrip, found 12 hours ago
$150
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Mon, Oct 26 from Hartsfield-Jackson Atlanta Intl. to Pensacola Intl., returning Mon, Nov 2, priced at $150 found 12 hours ago
Sun Country Airlines
Tue, Feb 23 - Thu, Mar 4
MSP
Minneapolis - St. Paul Intl.
VPS
Northwest Florida Regional
$196 Roundtrip, found 18 hours ago
$196
Roundtrip
found 18 hours ago
Select Sun Country Airlines flight, departing Tue, Feb 23 from Minneapolis - St. Paul Intl. to Northwest Florida Regional, returning Thu, Mar 4, priced at $196 found 18 hours ago
Allegiant Air
Sat, Oct 17 - Wed, Oct 21
IND
Indianapolis Intl.
VPS
Northwest Florida Regional
$205 Roundtrip, found 1 day ago
$205
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Sat, Oct 17 from Indianapolis Intl. to Northwest Florida Regional, returning Wed, Oct 21, priced at $205 found 1 day ago
Frontier Airlines
Sat, Oct 17 - Thu, Oct 22
MSP
Minneapolis - St. Paul Intl.
PNS
Pensacola Intl.
$244 Roundtrip, found 18 hours ago
$244
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Sat, Oct 17 from Minneapolis - St. Paul Intl. to Pensacola Intl., returning Thu, Oct 22, priced at $244 found 18 hours ago