Little Chicago Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Little Chicago Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hyatt Regency Minneapolis

Hyatt Regency Minneapolis

4 out of 5
Downtown Minneapolis
Price was CA $1,058, price is now CA $884 per person
CA $884
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Minneapolis (MSP)
9/10 Wonderful! (1,003 reviews)

The Marquette Hotel, Curio Collection by Hilton

The Marquette Hotel, Curio Collection by Hilton

4.5 out of 5
Downtown Minneapolis
Price was CA $1,299, price is now CA $1,097 per person
CA $1,097
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Minneapolis (MSP)
9.4/10 Exceptional! (1,002 reviews)
We loved our stay here. We stayed in an executive suite and had a beautiful view, very spacious room and bathroom. The bathroom was beautiful, lighting in there was great (so good for makeup) and the hotel hair dryer actually worked amazing. Location was great, walking distance to breakfast spots, target and a walgreens, Staff were very helpful and the overall hotel was beautiful and clean.

Reviewed on Oct 31, 2026

Emery, Autograph Collection Hotel

Emery, Autograph Collection Hotel

4.5 out of 5
Downtown Minneapolis
Price was CA $1,075, price is now CA $908 per person
CA $908
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Minneapolis (MSP)
9.4/10 Exceptional! (871 reviews)
Staff was very friendly and helpful. Location was ideal and very walkable for our purpose. Room was clean but not cozy. Very industrial decor, which is not our style. Bed wasn’t very comfortable but it also wasn’t the worst. Bathroom was spacious and clean. Overall, the room was lacking for a 4.5 star “luxury” hotel and the cost.

Reviewed on Oct 28, 2026

Nicollet Island Inn

Nicollet Island Inn

2.5 out of 5
Nicollet Island
Price was CA $1,142, price is now CA $975 per person
CA $975
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Minneapolis (MSP)
9.2/10 Wonderful! (108 reviews)

Hotel Ivy, a Luxury Collection Hotel, Minneapolis

Hotel Ivy, a Luxury Collection Hotel, Minneapolis

4.5 out of 5
Downtown Minneapolis
Price was CA $1,405, price is now CA $1,220 per person
CA $1,220
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Minneapolis (MSP)
9/10 Wonderful! (947 reviews)

Ready to book your vacation to Little Chicago?

 

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Little Chicago Hotel Deals

GrandStay Hotel and Conference

GrandStay Hotel and Conference

3 out of 5
7083 153rd St W Apple Valley MN
Fully refundableReserve now, pay when you stay
The price is CA $110 per night from Dec 1 to Dec 2
CA $110
CA $122 total
Dec 1 - Dec 2
includes taxes & fees
GrandStay Hotel and Conference
Lakeville Inn

Lakeville Inn

2.5 out of 5
20851 Keokuk Ave Lakeville MN
Fully refundableReserve now, pay when you stay
The price is CA $131 per night from Nov 8 to Nov 9
CA $131
CA $146 total
Nov 8 - Nov 9
includes taxes & fees
Lakeville Inn
Motel 6 Lakeville, MN - South - Lakeville

Motel 6 Lakeville, MN - South - Lakeville

2 out of 5
11274 210th St W Lakeville MN
The price is CA $78 per night from Nov 5 to Nov 6
CA $78
CA $87 total
Nov 5 - Nov 6
includes taxes & fees
Motel 6 Lakeville, MN - South - Lakeville
See all 124 properties in Little Chicago
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Little Chicago vacation package cost?
Cross off another part of the world with our Little Chicago vacation packages, which start from just CA $884. Select the hotels and flights that suit your travel style. Then, add on a few enriching experiences to cap off your unique getaway.
How do I get a cheap travel package to Little Chicago?
Our Little Chicago vacation packages offer plenty of savings for the savvy globetrotter. For the best deal, simply combine your flights, hotels and extras (including tours) into a budget-friendly package. But low prices are only the start of your next awesome adventure. Book with Expedia and and you'll have over 550 air carriers and 1,000,000 hotel options throughout the world to pick from. Whatever your budget or style, there's a vacation package that's perfect for you.
How far in advance should I book my Little Chicago vacation?
Travelers are generally able to browse international flights on Expedia within 12 months of departure. Booking last minute? With a bit of luck, it's still possible to score an affordable ticket just weeks before your flight.
What does an Expedia Little Chicago travel package include?
Hotels, rental cars and flights — we have them covered. With Expedia, you can shape your Little Chicago travel package your way. All you have to do is figure out what you need. Once you've made your booking, you can add on extras like experiences and activities. The more you bundle, the greater the savings!
What should I know before booking a Little Chicago travel package?
So many places to travel to, so many things to see and do. With a package, you'll be able to cross more of them off your list. Bundle your hotels, rental cars and flights and see how much you save.
Can I choose my airline with a Little Chicago Expedia vacation package?
Yes, of course. Expedia has access to more than 550 partner airlines all over the world, so select the carrier that best suits your travel needs.
If I'm not able to travel, can I cancel my Little Chicago vacation package?
You can. We totally understand that life doesn't always go to plan, so we're happy to help if you have to make changes to your Little Chicago vacation package. It may be possible to cancel or amend your itinerary for free if you've booked in the last 24 hours. Your hotel, airline or car rental company may charge you a fee if your booking was made more than 24 hours ago. Take a look at our Customer Service Portal for more information. Also, be sure to check your itinerary for the nitty-gritty on change fees.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.