Rogers Park Vacation Packages

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Top Holiday Package Deals in Rogers Park

Price found within the past 48 hours. Click for updated prices.
Baymont by Wyndham Glenview

Baymont by Wyndham Glenview

3 out of 5
Price was CA $768, price is now CA $557 per person
CA $557
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
7.6/10 Good! (1,004 reviews)
Breakfast was there but not a lot Look at moving in individuals using it as a home Good location though nice area around the place

Reviewed on May 9, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $2,632, price is now CA $1,645 per person
CA $1,645
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
The view is fantastic. You can see the Chicago river on one side, abd skyscraper on tge other side. The small items that the hotel provides, makes the stay, pleasant and homely.

Reviewed on May 10, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $2,355, price is now CA $1,579 per person
CA $1,579
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
If you plan on staying in this hotel by all means the view is great, but if you plan on moving your vehicle at all the hotel does not validate In-N-Out parking. You have to pay every time you want to leave and come back. Unlike the normal hotel, La Quinta downtown Chicago validate parking yes it’s $70 but you can drive in and out as many times as you want during your stay. Unlike this hotel.

Reviewed on May 8, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,700, price is now CA $1,206 per person
CA $1,206
per person
Jun 25 - Jun 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,124 reviews)
Great staff and perfect place to be in the middle of everything!

Reviewed on Apr 27, 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Price was CA $1,874, price is now CA $1,364 per person
CA $1,364
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Beautiful property. Convenient location for anything in the Loop area. Love the coffee and wine hours. Great restaurant in Boleo, too!

Reviewed on May 5, 2026

Where to stay in Rogers Park

Find the best Rogers Park areas and neighborhoods for the activities you enjoy most. Learn more about Rogers Park
Downtown Chicago

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Rogers Park Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $183 per night from May 12 to May 13
CA $183
CA $217 total
May 12 - May 13
includes taxes & fees
8/10 Very Good! (10,207 reviews)
Clean room, good staff

Reviewed on May 11, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $193 per night from May 25 to May 26
CA $193
CA $269 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (4,106 reviews)
Was a really nice hotel. My only concerns was the phones in the room didn’t work. No way to call front desk, front people weren’t super helpful and there was no microwave. Rooftop bar and room were excellent

Reviewed on May 10, 2026

Hotel Riu Plaza Chicago
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $178 per night from May 25 to May 26
CA $178
CA $212 total
May 25 - May 26
includes taxes & fees
9/10 Wonderful! (4,293 reviews)
The hotel staff is excellent! Very friendly and very helpful. The hotel is very clean and well maintained. The only issue I had was the charging ports and electrical sockets next to our bed did not work which made overnight charging of our phones and watches difficult.

Reviewed on May 10, 2026

Hilton Chicago/Magnificent Mile Suites
See all 4,642 properties in Rogers Park
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.
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Frequently asked questions

How much does a Rogers Park vacation package cost?
Be ready to book, because a trip to Rogers Park starts from a tempting CA $557. When you combine your flights, hotels and car rentals into a vacation package, you'll walk away with the biggest bargains.
How do I get a cheap travel package to Rogers Park?
Browse and book everything in one place with our Rogers Park vacation packages. You'll find deals on hotels, flights, tours and more that'll keep your pocket happy and your spirit of adventure alive. And, with more than 550 partner airlines and 1,000,000 hotel options all over the world to pick from, you'll have endless opportunities to mix and match all you want.
Where should I stay in Rogers Park?
Tick Lincoln Park off your bucket list and then stay right around the corner. Experience the exciting vibe around this famous attraction and visit whenever you like!
What are the top hotels in Rogers Park?
Hampton Inn Chicago North-Loyola Station and Super 8 by Wyndham Chicago IL are among the most sought-after hotels in Rogers Park. Why not look up the facilities and rates at each and then make a decision?
How far in advance should I book my Rogers Park vacation?
While not all air carriers advertise ticket prices early, it's usually possible to start comparing international airfares on Expedia up to a year in advance. This is the time when you'll nab some incredible bargains. If you've left things to the last minute, you might still be in luck. Discounted prices occasionally appear a few weeks before departure.
What does an Expedia Rogers Park travel package include?
Packages include flights, rental cars and hotels, but you can mix and match them to create your perfect Rogers Park trip. You can also add on fun stuff like activities and experiences once you've made your booking. You're in control! When you bundle your bookings with Expedia, you'll enjoy discounts you won't find anywhere else.
What should I know before booking a Rogers Park travel package?
A package can be easier on the credit card than separately booking all you need for your adventure. For example, combine your flights, hotels and rental cars and score impressive savings. No matter your vacation plans, you'll find a package that fits your budget.
Can I choose my airline with a Rogers Park Expedia vacation package?
Yes — that's the beauty of an Expedia vacation package. You're in control. We have more than 550 airline partners across the globe, so you have options galore when organizing your Rogers Park escape.
If I'm not able to travel, can I cancel my Rogers Park vacation package?
Your situation can change in a flash, so yes, you can. You may be able to amend or cancel your Rogers Park vacation package for free within 24 hours of booking. For older bookings, you can still cancel and rebook, but your airline, hotel or car rental company may impose a charge. Looking for more information? Visit our Customer Service Portal. We'll help make sure your trip goes off without a hitch.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

CA $55
per adult
94% of travellers recommend
Art Institute of Chicago
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $61
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.