Niles 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

Your Niles Vacation

From its small-town feel to its family-friendly attractions and beyond, there's lots to love about Niles. Uncover the wonders of this awesome city with a Niles vacation package that's customized for you. Fill up your itinerary with visits to Allstate Arena, Rosemont Theatre and Fashion Outlets of Chicago, some of the attractions you just have to see during a trip to Niles. Expedia has what you need to escape your daily routine. Tailor your vacation to Niles to match your travel style, whatever that may be.

Top Niles Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,443, price is now CA $1,038 per person
CA $1,038
per person
Aug 6 - Aug 9
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

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

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was CA $1,662, price is now CA $1,076 per person
CA $1,076
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,137 reviews)
Keep an eye that nothing is added from the minibar but great property and can't wait to stay again!

Reviewed on May 5, 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

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,628, price is now CA $1,096 per person
CA $1,096
per person
Jun 26 - Jun 30
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (471 reviews)
The rooms were very clean!

Reviewed on May 4, 2026

Ready to book your vacation to Niles?

 

Choose your dates

Niles 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! (10,209 reviews)
Parking lot nearby - no coffe bar - in room coffee machine didn’t work. Good location for walking to Grant Park

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 $204 per night from May 25 to May 26
CA $204
CA $281 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 $204 per night from May 25 to May 26
CA $204
CA $243 total
May 25 - May 26
includes taxes & fees
9/10 Wonderful! (4,294 reviews)
Amazing 😍😍😍😍. I would definitely recommend

Reviewed on May 11, 2026

Hilton Chicago/Magnificent Mile Suites
See all 5,020 properties in Niles
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

Discover the most popular places to visit in Niles

Wrigley Field

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Niles

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 Niles

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.