Best Travel Insurance Firms in Winnipeg
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The 5 Best Travel Insurance Firms in Winnipeg

Travel insurance is often an overlooked aspect of planning for a vacation. Anyone who’s planning a vacation understands that it’s an overwhelming task, so oftentimes vacationers leave this out of their plans, regardless of how important it is.

Vacationers need to understand that bad things can happen during vacations. It’s all fun and games until an incident happens that ruins a relaxing getaway.

To lower this risk, people invest in travel insurance to ensure their safety. There are plenty of issues that may occur during a trip, and insurance can help cushion the costs.

Fortunately, there are quite a lot of insurance agencies in Winnipeg. In this article, we’ll be going through the best agencies we’ve found that offer reliable travel insurance.

The Best Travel Insurance Firms in Winnipeg

We’ve browsed through various insurance agencies found in Winnipeg, and we’ve determined that these five agencies can offer the best deal for your travel insurance needs.

We’ve based our selection on key criteria you would normally expect from a decent insurance provider. The following brokers are judged based on the quality of the following:

Insurance Packages – To ensure that travelers get their money’s worth, great travel agencies should have a wide variety of travel insurance packages with corresponding promos and deals.
Comprehensiveness – Great travel insurance agencies should be able to provide insurance plans that cover a wide variety of risks involved in travel. Insurance firms need to provide emergency services to mitigate accidents that may happen overseas.
Availability – You never know when disaster may strike, insurance brokers with very flexible office hours will be easier for travelers to contact.
Customer Support – Great insurance firms need to have an impeccable customer support system. They will often deal with travelers in distress and therefore, should be able to address their needs effectively.

1. Medi-Quote Insurance Brokers

Medi-Quote Insurance Brokers
PRODUCTSTravel insurance, student insurance, health insurance, expatriate insurance, trip cancellations and interruptions, snowbird insurance, health insurance, and dental insurance
ADDRESS505 Pandora Avenue West, R2C 1M8
CONTACT DETAILSPhone: (204) 947-9210
OPERATING HOURSMonday to Friday: 9:00 AM - 4:00 PM
Insurance Packages★★★★☆ (4/5)
Variety★★★★★ (5/5)
Promos★★☆☆☆ (2/5)
Comprehensiveness★★★★★ (5/5)
Coverage★★★★★ (5/5)
Emergency Services★★★★★ (5/5)
Availability★★★☆☆ (3/5)
Customer Support★★★★★ (5/5)

A noticeable aspect while browsing Medi-Quote’s website is they position themselves as a brokerage firm that helps you purchase the right insurance plan, not simply a vendor.

They have access to a wide variety of travel insurance packages that cater to anyone’s unique travel coverage needs. MediQuote gives its clients the option to customize their insurance policies to fit whatever benefits they would want out of their plans.

Their travel insurance packages cover the usual benefits you’d expect from an insurance package. Their plans include cancellation for non-refundable trips, flight delays, trip interruptions, lost baggage, health and dental, and pre-existing medical conditions.

Other than this, they’ve also packaged insurance policies that are specifically designed for expatriates, traveling students, and frequent flyers.

Their website is easy to browse, although they failed to show rates for their insurance packages. Instead, they rely on a quotation system that some may find hard to use.

They set themselves apart by being a firm that’s willing to educate in all matters related to travel and medical insurance. The brokerage firm is very proud of its personalized approach to customer care that makes sure they are within an arm’s reach of their clients in case their services are needed.


  • Offers a wide variety of insurance packages
  • Products can be customized to fit the traveler’s plans and needs
  • Friendly, efficient, and thorough customer support team


  • Only has a single branch in Winnipeg
  • Cumbersome quotation process, the website lacks transparency
  • Online app can be difficult to use, based on feedback from elderly clients

Customer Reviews

A very responsive and reliable insurance team

Was referred to Medi-Quote by a family member to purchase Covid insurance for a family vacation. Was very impressed with the responsiveness of the fellow I spoke with as well as the clarity he provided on the coverage for our family. Had discussed this previously with 2 other companies and the service provided by Medi-Quote was far and away from the best. 10/10. Ended up purchasing trip cancellation insurance as well and thankfully didn’t have to use any of it. Would highly recommend it. – Cameron Junck

A very convenient and pleasing firm to deal with

Medi-Quote was very easy to deal with in my purchase of travel insurance. They were quick to respond to my request and very thorough with their answers. They also offered options regarding what (or whatnot) to purchase. We were also pleased with the pricing. – Chris Riddell

2. Group Medical Service (GMS) Canada

Group Medical Service (GMS) Canada
PRODUCTSHome insurance, commercial insurance, agricultural insurance, auto insurance, financial services, travel, and health insurance
ADDRESS298 Lanark St, Winnipeg, MB, R3N 1L2
CONTACT DETAILSPhone: (204) 489-9140
OPERATING HOURSMonday to Friday: 7:00 AM - 6:00 PM
Insurance Packages★★★★☆ (4/5)
Variety★★★★☆ (4/5)
Promos★★★☆☆ (3/5)
Comprehensiveness★★★★★ (5/5)
Coverage★★★★★ (5/5)
Emergency Services★★★★★ (5/5)
Availability★★★☆☆ (3/5)
Customer Support★★★★★ (5/5)

Group Medical Service or GMS has been in the service of providing coverage for quality healthcare since 1949. It’s considered one of the pioneers in providing healthcare coverage for medical services that are not subsidized by the government.

They began their tenure in the insurance industry offering medical insurance, but they have since expanded to include group and employee benefits, and travel insurance. Their travel insurance packages under their TravelStar program are customizable to fit your travel needs.

They offer a variety of travel insurance packages that are specifically designed for certain flyers. GMS has policies that cater to students, immigrants, and visitors to Canada.

These policies can cover up to $5,000,000 in medical expenses and include emergency medical services. GMS also offers virtual care and consultation for minor injuries that may occur during your trip.

Unfortunately, due to the global pandemic, they only have limited coverage for their student plans under the TravelStar program. Also, it’s indicated in their fine print that their policies are non-refundable once paid for.

But aside from the no-refund aspect, their policies and terms are transparently shown on their website. They indicate the full coverage of their insurance plans and have even added a quick quotation feature for clients to have an idea of how much their personalized insurance plan might cost.


  • Good for families
  • Offers student immigrant and visitor insurance plans
  • Customizable travel insurance


  • Non-refundable plans
  • TravelStar and Student Insurance under limited availability due to pandemic

Customer Reviews

Speedy reimbursement for claims

Friendly and insightful staff. Quick on claims reimbursements. Would highly recommend to anyone seeking Personal/Group Health & Dental Insurance or Travel Insurance. – Regina Cougar Hockey Alumni

A very reliable insurance firm with great people and service

I want to say this loud enough that their CEO hears this. If you, an insurance customer, like supporting a company that takes care of their staff when they need their help, let Group Medical Services take care of you. Great organization. Great people. A formula that creates a great work environment. Thank you GMS. Thank you for looking after my wife. You really are an outstanding organization. – Bob Johnson

3. Crossroads Insurance

Crossroads Insurance
PRODUCTSCondo insurance, travel insurance, cottage insurance, tenant insurance, business insurance, home insurance, auto insurance, life insurance
ADDRESSSt. Vital: 2 - 851 Dakota St. Winnipeg, MB R2M 5M2 Canada Tyndall Park: 850 Keewatin Street Winnipeg, MB R2R 0Z5 Canada
CONTACT DETAILSSt. Vital: 204.257.3076

Tyndall Park: 204.953.4000

OPERATING HOURSMonday to Friday: 9:00 AM - 5:00 PM

Saturday: 10:00 AM - 4:00 PM

Insurance Packages★★★★☆ (4/5)
Variety★★★☆☆ (3/5)
Promos★★★★★ (5/5)
Comprehensiveness★★★★★ (5/5)
Coverage★★★★★ (5/5)
Emergency Services★★★★★ (5/5)
Availability★★★★☆ (4/5)
Customer Support★★★★★ (5/5)

Crossroads is a comparably smaller insurance firm found in Winnipeg. It’s been run by the McRedmond family since 1972 and has since expanded to have two offices in Winnipeg that offer a myriad of insurance policies mainly from Blue Cross and Allianz.

Compared to other insurance firms in this list, they have a comparatively small list of insurance plans indicated on their website.

They offer the typical coverage options you would expect from a travel insurance plan. This includes cancellations, travel emergencies, travel to Canada, student travel plans, lost baggage, and trip interruptions.

They also offer discounted packages for regular travelers, similar to Medi-Quote’s frequent flier packages. They’re more strict with travelers who are afflicted with pre-existing medical conditions and screen these individuals more thoroughly.

Similar to other firms in this list, their insurance policies are not directly visible on their website. They also failed to include standard pricing or product comparisons that would have been useful for clients.

As a small firm, it’s unsurprising that they’re known for convenient and efficient customer service. They have been recognized for their ability to adequately respond to clients and their efficiency to fulfill insurance claims.


  • Friendly and knowledgeable staff
  • Fast service
  • Well-designed website
  • Convenient office hours


  • Product specifics are not immediately visible on the website
  • Limited selection of products compared to the other companies listed

Customer Reviews

An insurance broker worth going back to

I have been dealing at Crossroads Insurance for many years…and particularly with Tiana M. Every time I had insurance or MPI-related questions, Tiana provided detailed and immediate information…and also took the time to discuss options and additional advice. She is extremely professional and at the same time makes the transaction fun and enjoyable! She is super friendly and makes you feel at ease with any transaction you need to complete. She is uber-efficient and genuine in her role as an advisor. I have recently moved and, even from another province, she is quick to jump to my assistance to help make the transition seamless and painless. I wish I had a Tiana at my insurance location in my new province!!! 6 Stars!!! – Kelly Rock

Our preferred insurance partner for over 3 years

I have been dealing with Cody Malcolm of Crossroads insurance for the past 3 years. I cannot provide enough positive feedback on how he has conducted his business with me. He is professional, knowledgeable, adaptable, and very prompt in returning messages but even more importantly he always provides a personal human element to each interaction. As a commercial provider, he has exceeded my needs for information and products but he has also taken the time to assist me in my home policies. He is always pleasant to deal with. I maintain a small list of contacts I would refer to as family and friends and Cody would top that list. If there was a way to give more than 5 stars I would. Thanks again for all past services and I look forward to future business with you and Crossroads. – Dan Arnal

4. CAA Manitoba

CAA Manitoba
PRODUCTSTravel insurance, travel services, automobile insurance, roadside assistance, property insurance, health and dental insurance, pet insurance, life insurance
ADDRESSEmpress 870 Empress Street, Winnipeg, R3G 3H3 Kildonan Place 1555 Regent Avenue W., Winnipeg, R2C 4J2 St. Anne’s 501 St. Anne's Road, Winnipeg, R2M 3E5 Brandon Unit C, 305 18th Street N., Brandon, R7A 6Z2


Kildonan Place: Phone:


St. Anne’s: Phone:


Brandon: Phone:


OPERATING HOURSMonday to Friday: 10:00 AM - 5:00 PM

Saturday and Sunday: Closed

Insurance Packages★★★★★ (5/5)
Variety★★★★★ (5/5)
Promos★★★★★ (5/5)
Comprehensiveness★★★★☆ (4/5)
Coverage★★★★☆ (4/5)
Emergency Services★★★★☆ (4/5)
Availability★★★★★ (5/5)
Customer Support★★★☆☆ (3/5)

CAA Manitoba is one of the oldest insurance service providers in Canada. It is a non-profit association that was established over 115 years ago that specializes in auto assistance and roadside service.

It has grown as an association and now has the capacity to provide several insurance packages and benefits. Their menu of products includes roadside services and a variety of insurance policies such as property insurance, travel insurance, pet insurance, health and dental insurance, and life insurance.

What sets CAA Manitoba apart from its competitors is their membership program that opens customers to a myriad of perks, benefits, and discounts for their insurance plans and other protection services.

They have a decent catalogue of travel insurance plans that suit a variety of travellers. These plans are fully customizable and include the usual benefits that come with travel insurance including baggage protection, health and dental benefits, cancellations and trip interruptions, and emergency services.

Aside from this, CAA members are also entitled to CAA’s travel agent services. This essentially makes the association an all-in-one shop for a traveller’s trip or vacation needs.

They do not explicitly state the price of their insurance packages. However, they do have a user-friendly insurance calculator to give travellers a baseline cost for their preferred insurance plan.

Clients have also stated that they have comparatively cheaper insurance rates compared to other providers.


  • Offers exclusive insurance discounts for members
  • Offers exclusive perks for members
  • Also operates as a travel agent
  • Cheaper than others based on reviews


  • Customer service varies from branch to branch

Customer Reviews

An exceptional insurance firm

I’ve been here twice for vacation insurance and both times it was perfect. Helpful and knowledgeable staff answer all my questions and never try to rush you even if its busy. I know where I’m going for trip insurance in the future! – Jerid Rathore

Efficient and friendly staff providing good insurance

I was able to get fast travel insurance when I had to make a quick trip to the USA. Friendly and efficient. – Margaret D

5. Manitoba Blue Cross

Manitoba Blue Cross
PRODUCTSHealth insurance, life insurance, group and company insurance, travel insurance, disability management, retiree support
ADDRESS599 Empress Street, Winnipeg, Manitoba
CONTACT DETAILSPhone: 204.775.0151

Monday to Friday: 9:00 AM - 4:00 PM

Weekends: Closed

Call Center

Monday to Friday: 8:00 AM - 5:30 PM

Weekends: Closed

Insurance Packages★★★★☆ (4/5)
Variety★★★★☆ (4/5)
Promos★★★★☆ (4/5)
Comprehensiveness★★★★★ (5/5)
Coverage★★★★☆ (4/5)
Emergency Services★★★★★ (5/5)
Availability★★☆☆☆ (2/5)
Customer Support★★★★☆ (4/5)

Among the firms joined in this list, Manitoba Blue Cross is undoubtedly the most familiar. They’re an award-winning firm that offers comprehensive insurance policies that they make accessible to individuals and independent insurance firms.

The history of Blue Cross is deeply rooted in healthcare and has had over 80 years of experience in the industry. As such, they’re recognized as one of Canada’s most reliable health benefit providers.

They have a very thorough website that lists down everything a traveler needs to know about various insurance policies and their benefits.

Blue Cross also has a large selection of policies with a complete list of benefits tabulated so you can compare insurance policies with each other.

Their travel insurance packages include emergency support, international travel assistance, and repatriation. Unfortunately, their basic insurance plans don’t cover airfare, prepaid travel expenses, or trip cancellation, and not all of their plans include baggage protection.

It’s worth noting that they only have one branch in Winnipeg. As such, they’re not that accessible. And among their reviews, many have complained that the firm has a complicated procedure for applying for a policy and claiming benefits.


  • Carries a variety of plans for travelers including emergency health coverage and trip cancellation insurance
  • Website has an interactive tool to compare different plans
  • Offers group insurance plans


  • Complicated procedures for filing
  • Some plans have limited coverage
  • Only one branch in Winnipeg
  • Policies are non-refundable

Customer Reviews

Light and straightforward firm to deal with

Had to call in for support on a claim. The lady I got on the line was FANTASTIC. Appreciated her being straightforward yet friendly, and having a laugh with me. Keep it light where appropriate. She solved my problem and I got paid in the end – Jason Skinner

A breeze to deal with, just schedule to avoid lines

The process was quick and easy. Very accommodating. You have to pick your day though……it was so busy one day I couldn’t wait. Check the hours too. Closed to the public Mondays. Opens at 10 a.m., I think. – Janet Elsey

FAQs about Travel Insurance in Winnipeg

And that’s all there is to it. Hopefully, this list has guided you through the complicated process of finding the best travel insurance firms and plans for you.

Having the best experience and security for your trip is essential if you want to truly enjoy your vacation. That includes a partnership with a travel insurance broker that can cover your travel needs effectively.

If you’d like to know more about other insurance brokers in the city, then you can check out our list of the best insurance brokers in Winnipeg and skim through their various terms and policies for any of your other insurance needs.

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