Playin Hooky Charters 

4.6/5 (10 reviews)
 South Harbor Place 55, Waukegan, IL 60085, United States

Playin Hooky Charters 

4.6/5 (10 reviews)
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South Harbor Place 55
Waukegan, IL, United States

Book your next trip with Playin’ Hooky Charters and find out what keeps anglers coming back to Waukegan, Lake Michigan, located within 30 miles of Chicago, for more!

These waters are known for Brown Trout, Coho Salmon, Chinook Salmon, Rainbow Trout (Steelhead), Lake Trout, and more – with any luck, you’ll hook into a few! Depending on the species you’re after, you may find yourself light tackle fishing, trolling, or maybe something more specialized in this area.

Trips with Playin’ Hooky Charters are open to the whole family, so feel free to make a family day out of it! Be sure to ask if child-sized life vests are available, otherwise you should bring your own. You’re welcome to bring snacks to stay fueled throughout your trip!

Your adventure begins aboard a 33’ Pacemaker sportfishing vessel that can carry up to 6 passengers. It has downriggers and all the essentials. There’s a toilet on board for your convenience. Your captain will provide rods and reels, along with lures.

A 10–20% tip is customary to show your appreciation for their hard work.

You will need to buy a local fishing license before the trip. This information is usually available online, or you can ask the captain. Some species may be off-limits or require a special tag, so make sure you know what to expect.

A few items to bring include sunblock (non-spray), bottled water, and sunglasses. Alcohol is allowed in moderation, just avoid hard liquor as well as glass bottles.

You could keep reading this, but wouldn’t you rather be fishing with Playin’ Hooky Charters?

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Customer reviews

Rating summary

4.6/5
out of 5 stars from 10 reviews
Boat
4.5/5
Crew
4.6/5
Experience
4.6/5

Photos & videos by reviewers (7)

Choose a different time of year
August fishing trip
May fishing trip
+4

Angler rating

6
1
1
0
0

Anglers claimed

Good experience

100%

Appropriate for children

100%

Friendly captain

100%

Satisfied with the boat

100%

Recommend this charter

55%

Caught fish

100%

Showing 1 - 5 of 11 reviews
Showing: 5 of 11 reviews
Daniel E.
Daniel E.

Jul 19, 2025

The captain canceled

VERIFIED

The charter operator canceled on trip date. This is an automated posting.

 


Dainius G.
Dainius G.
5.0/5

Aug 2, 2025

5 Hour Trip (AM)

August fishing trip

VERIFIED

 

Review media 0
 Dainius G. recommends Playin Hooky Charters
 Dainius G. recommends Playin Hooky Charters

Anthony W.
Anthony W.
5.0/5

Jun 26, 2025

5 Hour Trip – Weekday Special

Great time!

VERIFIED

 

 Anthony W. recommends Playin Hooky Charters
1 person finds this review helpful
 Anthony W. recommends Playin Hooky Charters
1 person finds this review helpful

Kenneth K.
Kenneth K.
4.7/5

May 5, 2025

5 Hour Trip – Weekday Special

May fishing trip

VERIFIED

 

Captain replied
 Kenneth K. recommends Playin Hooky Charters
2 persons find this review helpful
 Kenneth K. recommends Playin Hooky Charters
2 persons find this review helpful
undefined (The Captain)
Replied on May 6, 2025
Thanks guys
Review media 0

Terry M.
Terry M.
5.0/5

Oct 19, 2024

5 Hour Trip (PM)

Amazing Time!

VERIFIED

We highly recommend Captin John! He is very knowledgeable and knows where the fish are. My family had the best time and we each caught a fish. We will be back hopefully next spring!

We highly recommend Captin John! He is very knowledgeable and knows where the fish are. My family had the best time and we each...  

Review media 0
 Terry M. recommends Playin Hooky Charters
1 person finds this review helpful
 Terry M. recommends Playin Hooky Charters
1 person finds this review helpful

Trip availability and prices

Trip Date:
Days:
Group Size:
Select date to see availability
October 2025
SuMoTuWeThFrSa
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Number of days
1
Group Size
2 adults • 0 children
Change
Almost there...
5 Hour Trip – Weekday Special
FREE Cancellation 7 days notice
5 Hour Trip, starts at 3:00 PM
Seasonal trip (Mon, Tue, Wed, Thu, Fri)
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US $575 
Entire boat: up to 6 people
5 Hour Trip (AM)
FREE Cancellation 7 days notice
5 Hour Trip, starts at 6:00 AM
Seasonal trip (Fri, Sat, Sun)
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US $800 
Entire boat: up to 6 people
5 Hour Trip (PM)
FREE Cancellation 7 days notice
5 Hour Trip, starts at 11:00 AM
Seasonal trip (Fri, Sat, Sun)
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US $800 
Entire boat: up to 6 people
6 Hour Trip (AM)
FREE Cancellation 7 days notice
6 Hour Trip, starts at 6:00 AM
Seasonal trip (Sat, Sun)
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US $840 
Entire boat: up to 6 people
6 Hour Trip (PM)
FREE Cancellation 7 days notice
6 Hour Trip, starts at 12:00 PM
Seasonal trip (Sat, Sun)
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US $840 
Entire boat: up to 6 people
Full Day Trip
FREE Cancellation 7 days notice
8 Hour Trip, starts at 6:00 AM
Seasonal trip (Sat, Sun)
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US $950 
Entire boat: up to 6 people
There is 1 person looking at this charter.

Customer reviews

Rating summary

4.6/5
out of 5 stars from 10 reviews
Boat
4.5/5
Crew
4.6/5
Experience
4.6/5

Photos & videos by reviewers (7)

Choose a different time of year
August fishing trip
May fishing trip
+4

Angler rating

6
1
1
0
0

Anglers claimed

Good experience

100%

Appropriate for children

100%

Friendly captain

100%

Satisfied with the boat

100%

Recommend this charter

55%

Caught fish

100%

Showing 1 - 5 of 11 reviews
Showing: 5 of 11 reviews
Daniel E.
Daniel E.

The captain canceled

VERIFIED

Trip was supposed to happen on July 19, 2025

The charter operator canceled on trip date. This is an automated posting.

 


Dainius G.
Dainius G.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

August fishing trip

VERIFIED

5 Hour Trip (AM) on August 2, 2025

 

Review media 0
 Dainius G. recommends Playin Hooky Charters

Anthony W.
Anthony W.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Great time!

VERIFIED

5 Hour Trip – Weekday Special on June 26, 2025

 

 Anthony W. recommends Playin Hooky Charters
1 person finds this review helpful

Kenneth K.
Kenneth K.
4.7/5

Experience:

4.0/5

Boat

5.0/5

Crew

5.0/5

Overall

May fishing trip

VERIFIED

5 Hour Trip – Weekday Special on May 5, 2025

 

 Kenneth K. recommends Playin Hooky Charters
2 persons find this review helpful
undefined (The Captain)
Replied on May 6, 2025
Thanks guys
Review media 0

Terry M.
Terry M.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Amazing Time!

VERIFIED

5 Hour Trip (PM) on October 19, 2024

We highly recommend Captin John! He is very knowledgeable and knows where the fish are. My family had the best time and we each caught a fish. We will be back hopefully next spring!

We highly recommend Captin John! He is very knowledgeable and knows where the fish are. My family had the best time and we each caught a fish. We will be back hopefully next spring!  

Review media 0
 Terry M. recommends Playin Hooky Charters
1 person finds this review helpful

FAQs about Playin Hooky Charters

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The fish you can target

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What is the boat like?

Boat Image
Boat category
Sportfishing boats
Capacity
6 persons
Boat length
33 ft
Year built
1980
Restored in
2014
Boat manufacturer
Pacemaker
Boat type
Sportfishing

Engine model
Omc
Powered by
2 x 270HP
Max cruising speed
20 knots
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