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Chicago Boat Tours Compared

Updated: December 22, 2023
 By Mel

This post compares the best discounts on Chicago boat tours and cruises, including architecture cruises, sightseeing tours, speedboats, sailboats, kayaks, and water taxis.


OVERVIEW

There are a lot of different river cruises and tours available in the city of Chicago, and this post provides links to the discounts available for each tour in the sections listed below.

There are several different types of discounts available which can help you save money in a variety of ways.

One of the most popular options is to purchase a tourist pass.

These services charge one flat price for access to dozens of popular attractions and activities, and they typically include at least a few cruises or boat tours.

Another option is to check popular discount sites like Groupon and LivingSocial to see if they are offering any deals on cruises or boat tours.

The advantage of these sites is they usually offer additional coupon codes to save even more money!

One of the most common discounts is group rates, and these special prices are only offered to people who are buying 20-40 tickets or more at once.

Some companies also offer discounts for seniors and military members, and there is at least one company that provides coupon codes.

If that’s not enough, there are a few companies that also offer free drinks!

In addition to covering prices and discounts, we'll also include details about which Chicago river cruise is best suited for each traveler.

While on a Chicago boat tour, you can expect excellent views and incredible city panoramas of the following attractions and well-known structures:

  • Grant Park
  • Goose Island
  • Trump Tower
  • Tribune Tower
  • Wrigley Building
  • Chicago Riverwalk
  • And more!

CHICAGO ARCHITECTURE TOUR DISCOUNTS

The windy city is home to the world’s first skyscraper, so it’s a pretty popular destination for anyone interested in the history of architecture.

There are currently 5 different ways to save money on an architecture boat tour in Chicago:

  • Free for kids
  • Tourist Pass
  • Group Rates
  • Discount Sites
  • Coupon Codes
Chicago River Boat Tours

You’ll enjoy the biggest possible discount by using a tourist pass but depending on when you check discount sites, you may find that they offer similarly excellent deals. 

For more details about these services, please read our full post covering Chicago Architecture Tours.

NOTE: Although we will list the most popular tour companies below, there might be a few we miss which are sold at a discount through websites like Groupon and LivingSocial.

If you can't find exactly what you're looking for, we recommend checking these discount sites to find a service that fits your needs and expectations.


SHORELINE ARCHITECTURE CRUISE

This company also provides a service covering some of the more notable architectural feats in Chicago.

While you wind your way down the river, you'll learn about the history of how this city recovered from the Great Fire of 1871 and see both older and newer examples of magnificent architecture.

Discover the role that architects such as Bertrand Goldberg, Jeanne Gang, and Mies van der Rohe played in creating the windy city that exists today.

Duration: 75 minutes

Prices

Location

This architectural cruise departs from either the Michigan Avenue or Navy Pier docks.

Discounts

The Shoreline company offers the following deals on its Architectural boat tour.


WENDELLA ARCHITECTURE CRUISE

This is another popular boat tour company in Chicago, and they offer a lot of great services, including a Lake and River Architecture Cruise.

One of the nice things about this tour is that it covers both the Chicago River and Lake Michigan, allowing you to see notable buildings on both sides of the city.

While you drift along the waters near Chicago, you'll learn all about the architectural history of the windy city from a professional guide providing in-depth commentary.

Duration: 90 minutes

Prices

Location

You will find a uniformed employee at the Michigan Avenue Bridge. When you present your ticket to this employee, they will guide you to the correct dock.

Discounts

This company offers a lot of different discounts, including some of the best deals of any service on our list.

  • Children under 4 are free.
  • 50% off on Tuesdays for College Students.
  • 50% off Mon - Thur for the Military and their spouses.
  • $10 off Mon - Thur for Veterans and Reservists.
  • Discounts not valid on Holidays.

And after reading this post, see which boat tours the roughly 17k members of our Chicago Travel Tips Facebook group say are their favorites and join the conversation.

The group is made up of locals, regular visitors to Chicago, and those just getting to know the city.

There's no need to join to read the recommendations.


SIGHTSEEING CRUISE DISCOUNTS

These services are all about discovering Chicago and learning about its history. Anyone looking for excellent photo ops will want to consider one of these river cruises.

Shoreline Sightseeing Cruises Chicago

Most of these boat tours offer some kind of narration describing the significant landmarks in the areas you will visit.

There are a total of 5 different discounts available on the following Chicago boat tours:

  • Tourist Pass
  • Discount Sites
  • Group Rates
  • Free for Kids
  • Coupon Code

The best opportunity to save is probably to purchase a tourist pass, but you might be able to get a comparable deal using a discount site.

NOTE: This section features the most popular tour companies, but there might be a few we miss which are sold at a discount through websites like Groupon and LivingSocial.

If you can't find exactly what you want, we recommend checking these discount sites to find a service that fits your expectations.


SHORELINE SIGHTSEEING CLASSIC LAKE TOUR

Shoreline has been offering tours since 1939, and their experience shows.

We highly recommend this guided, historic sightseeing tour on Lake Michigan.

Lake Cruise Shoreline Sightseeing Chicago

You can bet that your guide will have more than a few jokes as they describe Chicago history through the current landmarks along the waterfront.

Duration: 40 minutes

Prices

Location

Classic Lake Michigan Tours depart from West Dock Navy Pier, 600 E Grand Ave, across from McDonald’s (map).

Discounts

If you're looking to save money on this service, Shoreline offers the following deals:


KAYAK CHICAGO

Take a guided tour of Lake Michigan while paddling your own single or tandem kayak!

Perfect for beginners, this leisurely experience offers top-quality tours that Yelp users applaud for customer service and easily accommodating last-minute walk-ups.

Kayak Chicago River

They even allow dogs! This tour includes an orientation to paddling.

Duration: 2.5 hours

Price:

Discounts

This company doesn't offer a lot of discounts, but they do have coupon codes every now and then, so we recommend checking their site to see whether or not there are even more deals available.


SPEED BOAT TOUR DISCOUNTS

Anyone looking for fun and excitement on the Chicago River will want to consider a Speed Boat cruise.

These trips are more like a roller coaster ride than they are a boat tour.

As you ride through Chi-town at top speeds, you’ll see some of the most important landmarks in the city.

Guides will usually point out significant sights as you enjoy a thrilling experience.

There are only 3 ways to save money on these Chicago boat tours as of right now:

  • Group Rates
  • Kids are Free
  • Dog Discount

While the last option is definitely the strangest discount of them all, group rates are probably the best way to save money on these speed boat tours.

NOTE: You'll find the most popular speedboat companies below, there might be some we are missing which are sold at a discount through websites like Groupon and LivingSocial.

We recommend checking these discount sites if you can't find a service that fits your needs and expectations.


SEADOG’S LAKEFRONT SPEEDBOAT TOUR

If you’re looking to have some moderate thrills as you do your sightseeing, and you don’t mind the wind in your hair, we recommend Seadog.  

Race through the water as you hear about the Windy City’s most famous landmarks along the shoreline during their lakefront architectural tour.

Light and humorous, reviewers have a hard time knowing if they like the speed or the speeches more!

Beware: We see a pattern in the reviews of guests who are unhappy with the will-call ticket option due to long lines.

We recommend buying E-tickets in advance, which saves you from the long line and can help ensure you get a great seat by showing up about 20 minutes in advance.

Duration: 30 Minutes

Price (includes tax):

Location:

Depart from South Navy Pier, 600 E Grand Ave. (map). Look for the red & white ticket booth just across from the Ferris Wheel.

Discounts

The deals provided by this company are a bit different from what you'll find with other services, but at least you'll be able to save some money.

  • 15% off tickets if you bring your dog for the boat ride.
  • Special group rates are offered for Skydeck Chicago.
  • Children 2 and under are free.

CHICAGO WATER TAXI

If you don’t care about narration or tour guides, a water taxi might be the most affordable option on this list.

This outing is more about transporting you from one location to the next, but you can typically enjoy a lot of wonderful views while on the boat.

Chicago Water Taxi

There are only 3 different discount opportunities currently available on Chicago water taxis:

  • Senior Discount
  • Military Discount
  • Disability Discount

If you fit any of these categories, you’ll be able to save at least 50% on tickets. However, military members undoubtedly get the best deal, as they ride for free!

NOTE: We will list the most popular water taxi companies below, but there may be a few available through websites like Groupon and LivingSocial.

If you can't find exactly what you want, we recommend checking these discount sites to find a service that better fits your needs.


THE CHICAGO WATER TAXI

For a fast and cheap experience on the river, hopping on a water taxi can be a convenient way to travel for local commuters and travelers.

Many of Chicago’s popular attractions can be seen along these routes, and each of the station stops offer fantastic things to do, see, and eat.

NOTE: Due to the pandemic, Chicago Water Taxi is currently only available on Saturdays and Sundays. Cash is no longer accepted and you must purchase tickets with a debit or credit card.

While there are no guides on these boats, the sights are comparable to the ones on any of the sightseeing cruises listed above, and at a huge discount!

Duration: 15 to 30 minutes

Price Options:

Station Locations:

  • Ogilvie/Union Station (West Loop)
  • Michigan Avenue
  • LaSalle (River North)
  • Riverwalk Clark Street
  • North Avenue/Sheffield
  • Chinatown
  • Chicago Avenue

Discounts

There are a few deals available for senior citizens and members of the military. If this describes you, chances are you'll be able to save a lot of money on tickets.

  • 50% off one-way tickets for Seniors & people w/ Disabilities.
  • Active Duty military w/ ID ride for free.

SHORELINE WATER TAXI SERVICE

Another affordable taxiing service is Shoreline, which offers a route on the lake as well as the river.

We like this service for their unique lake route, which is the cheapest way to view the skyline while on Lake Michigan; notably the Museum campuses.

Duration: 15-40 minutes, depending on the chosen route.

Schedule:

  • May through September
  • Taxis operate 10 am-6 pm, at least every 20 minutes

Price Options and Packages:

There are no reservations for Shoreline taxis, as they are a commuter service. Tickets can be bought on-site.

Single Ride Extended River Route (Orange Line) | Lake Route (Green Line)

  • $16 - Adults 
  • $9 - Children

Single Ride River Route (Brown or Blue Line)

  • $10 - Adults
  • $5 - Children

Station Locations:

  • Union Station/Willis Tower
  • Navy Pier
  • Museum Campus
  • Michigan Avenue

NIGHT BOAT TOURS AND FIREWORK CRUISE DISCOUNTS

Like most metropolitan cities, Chicago looks entirely different after dark.

Several companies offer services at night, allowing you to get a good look at the lights from the city while you’re drifting down the river.

Some of these opportunities are only offered during the summer months, but they often include fireworks.

There are currently 3 different discounts available for the following Chicago night boat tours:

  • Group Rates
  • Discount Sites
  • Kids are Free

If you’re looking for the best opportunity to save money on a night boat tour or cruise, discount sites will likely provide your best chance at a good deal.

Major discount sites tend to feature all the latest fireworks and holiday cruises.

Depending on whether or not they have additional coupon codes, you could end up saving even more than you would with group rates.

NOTE: Although you'll find the most popular companies listed below, there might be a few we miss which are sold at a discount through websites like Groupon and LivingSocial.

If you can't find what you're looking for, consider checking these discount sites to find a service that fits your needs.


SHORELINE LAKE FIREWORK TOUR

Enjoy impressive views of Chicago’s skyline from Lake Michigan, with an uninterrupted view of the weekly fireworks display.

Tour-goers love to watch the reflection of the lights on the water, as well as the buildings!

Reviewers say to arrive at least 15 minutes prior to the tour’s start time, and this is well worth the money!

For a few extra dollars, many reviewers recommend taking Shoreline’s nighttime architecture fireworks tour (see below) which includes a guided view of the river.

Times:

Seasonal, May-September only.  

  • Saturdays 9:30 pm
  • Wednesdays 9:00 pm  

Duration: 60 minutes

Price(s):

Location:

Departs from Navy Pier West Dock, 600 E Grand Ave (map)

Discounts

As with their other services, the following deals are also available for their night/firework cruises.

  • Special group rates are available for 20 or more visitors.
  • Save 10% - 20% or more with Groupon/LivingSocial.
  • Children 2 and under are free.

SHORELINE ARCHITECTURE FIREWORK TOUR

Get all of the information on a daytime architecture tour, with an added grand finale: seeing fireworks on the lake!

No matter where you make your departures, you’ll tour the main and south branches of the Chicago River before traveling out onto the Great Lake for the best view of the weekly fireworks display.

Pro tip: Don’t forget your camera! Even though it is nighttime, the lights of the city offer perfect photo opportunities. You’ll have your postcard-worthy photo in no time!

Times:

Seasonal, May-September only. 

  • Saturdays 9:00 pm
  • Wednesdays 8:15 pm  

Duration: 90 minutes

Price(s):

Location:

Depart from one of two locations:

  • Navy Pier Entrance, Polk Bros Park. GPS: 600 E Grand Ave
  • Michigan Avenue Bridge (NE corner). GPS: 401 Michigan Ave

WENDELLA SUNSET CRUISE

In addition to their architectural boat tours, this company also offers an outing at sunset which allows you to enjoy excellent views of the city skyline.

This is intended to be a romantic cruise, so there won't be a lot of historic details about the city provided, but you will have the opportunity to enjoy a glass of wine, a cocktail, or a cold beer.

Since this is a sunset tour, you might not get to see Chicago after dark, but depending on the time of year, it's definitely a possibility.

Duration: 90 minutes

Prices

TIP: It's worth noting that this company offers specialty fireworks and holiday cruises to celebrate important events.

If you're visiting during the 4th of July or Christmas, check to see what holiday cruises they are currently offering.

Location

Wendella sends a uniformed employee to meet their guests at the Michigan Avenue Bridge. When you present your ticket, they will guide you to the correct dock.

Discounts

The same discounts they offer for their architectural cruises are also valid for their sunset cruises!

  • Children under 4 are free.
  • 50% off on Tuesdays for College Students.
  • 50% off Mon - Thur for the Military and their spouses.
  • $10 off Mon - Thur for Veterans and Reservists.

WINDY CITY SAILING

Windy City Sailing has led private yacht tours for 18 years, and recently added fireworks and special event packages.

Pro tip: Once the yacht is out of the harbor, ask for a chance to drive!

Duration: Flexible, minimum of 3 hours

Price:

$275 - $300 per hour| Hourly Rates

  • The Nebula, a 40-foot sloop-rig Beneteau sailboat

Discounts

This has offered their services through discount sites in the past. These websites sometimes offer discounts on local activities.


CHICAGO SAILBOAT CHARTERS  (NIGHTTIME OR FIREWORKS)

Want to try something different with friends, or surprise your significant other? Why not charter a sailboat and watch the fireworks on the lake!

Pack a picnic basket full of romantic food (BYoB) and watch the skyline light up. Don’t forget your camera!

Pro tip: While it might be tempting to wear flip-flops, for comfort and safety consider wearing non-slip shoes.

Fireworks: Wednesday and Saturday evenings, May through September.

Duration: Flexible, minimum of 3 hours

Price:

$599 and up | Hourly Rates based on vessel size and number of passengers:

  • Large (36’, up to 8 passengers)
  • Luxury (39’, up to 11 passengers)
  • Power Boat (40', up to 11 passengers) 
  • BIG Boat (up to 36 passengers)
  • Call 773-236-7245 for booking questions and special events.

Location: 400 W Belmont Harbor Dr

Discounts

This company changes its deals quite frequently, so we recommend checking its website to see what is currently available.


LUNCH AND DINNER CRUISE DISCOUNTS

In addition to the various night tours offered on Lake Michigan, you’ll also find a nice selection of dinner cruise options as well.

Instead of focusing on the excitement of a fireworks show, this boat trip is all about enjoying a meal while you drift alongside the city and experience the skyline in style.

There are a total of 3 different ways to save money on these services in Chicago:

  • Group Rates
  • Military Discount
  • Free Drink

Although the discounts available for these services aren’t always big, even 10% - 20% off an excursion that costs $100 on average is going to be a pretty good deal.

It’s also worth noting that the free drink offer from each company is likely one of the easiest discounts to enjoy.

NOTE: This section lists the most popular dinner cruise companies, but there might be a few we miss which are sold through websites like Groupon and LivingSocial.

If you can't find exactly what you need here, we recommend checking these discount sites to find a service that fits your expectations.


Odyssey Cruises

This is one of the most popular cruise companies in the United States. Their Chicago branch offers lunch, brunch, and dinner cruises.

The earlier the trip, the less you will pay for a ticket.

Most of their excursions include a three-course plated meal and wonderful music curated by an onboard DJ.

In comparison to their competition, this is definitely one of the more classy experiences you’ll have on Lake Michigan. Odyssey offers service pretty much year-round.

As one of the premiere cruise services in the Windy City, it shouldn’t come as too big of a surprise that they have earned a 4-star rating on TripAdvisor.

Although there are a few negative reviews, most customers were more than pleased with their trip.

Unhappy customers typically complained of uncommon issues that don’t represent the typical experience with Odyssey Cruises.

A majority of reviews came from passengers who were very impressed with the quality of their ship and the views at night in Chicago.

This dinner cruise is very popular with couples.


Discounts

There are a few different deals available when you choose this company, including opportunities to save on other popular activities.

  • Members of the Military will receive special rates w/ ID.
  • Get discounted group rates at Skydeck Chicago.
  • Receive 1 complimentary premium drink when you check in on Yelp.

Lunch Service

  • Ticket Price: $81.90 for Adults | $60.03 for Children
  • Duration: 2 hours

Brunch Service

  • Ticket Price: $117.44 for Adults | $92.83 for Children
  • Duration: 2 hours

Dinner Service

  • Ticket Price: $154.70 for Adults | $154.70 for Children
  • Duration: 3 hours

Schedule and more information


Spirit Cruises

Although this line is owned and operated by the same company as Odyssey, they actually offer a somewhat different experience.

Instead of a three-course plated meal, you’ll have the opportunity to enjoy a nice buffet while drifting along Lake Michigan.

In addition, they also provide entertainment in the form of DJ music and interactive games.

Unlike their classy counterpart, this service is all about having fun with friends and family.

Spirit offers lunch, brunch, and dinner cruises fairly often. Ticket prices are typically more affordable for these excursions.

Despite the differences between Odyssey and Spirit Cruises, this company has also received a 4-star rating on TripAdvisor.

There aren’t many negative reviews to speak of, but it’s worth noting that some passengers were unhappy with either the food or the customer service.

Thankfully, these comments do not represent the typical experience with their cruises.

An overwhelming majority of reviewers were very pleased with their trip, stating that the meal and entertainment they received were both excellent. 


Discounts

Much like the other dinner cruise companies on our list, this company also offers a variety of deals.

  • Military w/ ID will receive special rates.
  • Discounted group rates at Skydeck Chicago.
  • Get 1 complimentary premium drink by checking in on Yelp.

Lunch Service

  • Ticket Price: $68.77 for Adults | $52.37 for Children
  • Duration: 2 hours

Brunch Service

  • Ticket Price: $101.04 for Adults | $81.90 for Children
  • Duration: 2 hours

Dinner Service

  • Ticket Price: $125.63 - $125.63 per person
  • Duration: 2 ½ – 3 hours

Purchase tickets or learn more.


CHICAGO SAILBOAT AND KAYAK TOURS

When it comes to rest and relaxation, few boat tours are going to be as inviting as a sailboat. What better place to sail than the Windy City?

Enjoy the sights and sounds as you drift around the Chicago River in comfort.

There are 4 types of discounts available on these services in the Chicago area:

  • Tourist Pass
  • Group Rates
  • Discount Sites
  • Coupon Code

Without question, you’ll get the best possible deal on this service by using a tourist pass. That said, you may also find a similarly excellent deal on a discount site.

NOTE: This section will list the best sailboat companies below, but there may be a few which are sold at a discount through websites like Groupon and LivingSocial.

If you can't find what you want here, we recommend checking these discount sites to find a service that fits your expectations.


TALL SHIP WINDY

A true gem on the lake, Tall Ship Windy, and its billowing sails have all the allure of a pirate ship with modern conveniences to make your experience memorable.

Recent passengers say this is the most family-friendly experience they had on Navy Pier. Kids love the pirate ship, and adults love the full bar!

Pro tip: Don’t have the time or the budget to board Tall Ship Windy? While visiting this area, you can get up close and personal to admire its beauty while it is docked between tours.

Navy Pier offers many free and cheap activities for families on a budget.

Tour Theme Options:

  • Lakeside Architecture Sail (3 pm, 5 pm)
  • Real Pirates of the Inland Seas (1 pm)
  • Sunset Skyline Sail (7 pm)
  • Spirit Ships and Haunted Harbor

Duration: 75 minutes (arrive 30 minutes prior for boarding)

Price:

  • $49 - Adult
  • $39 - Child (under 13)

Purchase tickets or learn more.

Location: 600 E Grand Ave

Discounts

There is at least one additional opportunity to save money on these outings in addition to the deals you can also get on their night/firework cruises.

  • Group Discounts: 10% off for 20-39 people.
  • Group Discount: 15% off for 40-59 people.
  • Group Discount: 20% off for 60 or more people.
  • Check Groupon/LivingSocial to save 10% - 20% or more.

CHICAGO SAILBOAT CHARTERS (DAYTIME)

Looking to set sail privately? Consider these sailboat rentals, complete with your own Captain!

Highly rated for their customer service, your group can sail along our world-renowned shoreline knowing you are in good hands.

Pro tip: Don’t forget the cheese and wine! Charters allow snacks, including alcohol, onboard. Cups and ice provided.

Duration: Flexible, minimum of 3 hours

Price Range:

$599 and up | Hourly Rates based on vessel size and number of passengers.

Discounts

This company frequently changes up their deals from one season to the next, so we recommend checking their website to see what's available when you plan to go for a sail.


CHICAGO KAYAKS

If you’re looking for a more unique trip down the Chicago River, it’s hard to beat a kayaking tour!

Renting a one of these boats will get you closer to the water than any other option on our list.

You’ll also get a good workout while traveling around the city and enjoying wonderful views.

There are currently two different ways to save money on this type of service:

  • Coupon Codes
  • Discount Sites

The best option may in fact be discount sites, as they often offer additional coupon codes that you could use to save even more than usual!

NOTE: We will list the most popular tour companies below, but there might be a few we miss which are sold through websites like Groupon and LivingSocial.

If you can't find what you're looking for, check these discount sites to find a service that fits your needs.


KAYAK CHICAGO

Whether you want a guided tour of Lake Michigan, an Architectural tour on the Chicago River, or rent out kayaks (single or tandem!) for the day, this is a company you can trust.

Pro tip: Choosing to ride tandem (two people, one boat) saves you $10 off of the regular price of two kayaks, and allows one person to paddle while the other has their hands free to take photos!  

Prices for Rentals:

Price includes kayak, paddle, personal flotation device, and brief instruction.

  • Single $30/hr or $90/day
  • Double $40 /hr or $120/day

No reservations are needed. Questions? Call (312) 852-9258

Discounts

If you're looking to save money on this service, make sure to consider the following deals.

About The Author

Mel

Mel loves to be a tourist in her own city. With a background in performing arts, tourism, and photography, giving tours and being a story-teller comes naturally to her. She loves traveling, food, and theatre. Mel splits her time between Chicago and Los Angeles (#theatrelife) and leads tours and manages both cities!
Updated: December 22nd, 2023
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