Southwest Side Vacation Packages

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Top Southwest Side Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was CA $1,576, price is now CA $1,125 per person
CA $1,125
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
Nice hotel I would stay here again

Reviewed on Apr 15, 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 $1,895, price is now CA $1,259 per person
CA $1,259
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Breakfast and parking not included

Reviewed on Apr 12, 2026

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was CA $2,146, price is now CA $1,502 per person
CA $1,502
per person
Jul 6 - Jul 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
The best hotel I've ever stayed in. Please get an iron, please get a microwave. And please don’t charge for every single thing! ❤️

Reviewed on Apr 13, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,642, price is now CA $1,178 per person
CA $1,178
per person
Jul 6 - Jul 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (453 reviews)
This property never disappoints! The staff are awesome, particularly Nu at the front desk! Always very pleasant and friendly, provides awesome service every time we visit!

Reviewed on Apr 13, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,578, price is now CA $1,861 per person
CA $1,861
per person
Jul 6 - Jul 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
Beautiful facility, excellent service, professional staff, delicious food!

Reviewed on Apr 7, 2026

Where to stay in Southwest Side

Find the best Southwest Side areas and neighborhoods for the activities you enjoy most. Learn more about Southwest Side
artist paints mural on a city street

Back of the Yards

2 out of top 10 points of interest in this area

While Back of the Yards might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Bridgeport Art Center and Zhou B Art Center.

Find hotels in Back of the Yards

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Southwest Side 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 $170 per night from Apr 26 to Apr 27
CA $170
CA $200 total
Apr 26 - Apr 27
includes taxes & fees
8/10 Very Good! (10,147 reviews)
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Reviewed on Apr 14, 2026

Congress Plaza Hotel
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 $164 per night from Apr 26 to Apr 27
CA $164
CA $193 total
Apr 26 - Apr 27
includes taxes & fees
9/10 Wonderful! (4,123 reviews)
We stayed after seeing Hamilton at CIBC Easter weekend. The hotel was busy, but service was quick and representatives were very friendly. The remodeled pool was great for my 11 year old niece.

Reviewed on Apr 15, 2026

Hilton Chicago/Magnificent Mile Suites
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
The price is CA $191 per night from Apr 26 to Apr 27
CA $191
CA $224 total
Apr 26 - Apr 27
includes taxes & fees
8.6/10 Excellent! (5,839 reviews)
Breakfast was great compared to other hotels. The ac worked so that was good. The tv kept cutting off but i think it was because we were streaming so i wasnt too upset. Great staff!

Reviewed on Apr 15, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 5,110 properties in Southwest Side
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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Discover the most popular places to visit in Southwest Side

Wrigley Field

Wrigley Field

4.5/5(159 reviews)

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

4.5/5(3 reviews)

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

4.5/5(460 reviews)

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

Navy Pier

What to do in Southwest Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% 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 $60
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
See all activities in Southwest Side

Frequently asked questions

Can I cancel my flight booking to Southwest Side due to COVID-19?
Our handy Customer Service Portal is where you can get important information about canceling your Southwest Side flight due to COVID-19. Before you reserve a seat, it's smart to look over the terms and conditions of your airfare too.
What's the best way to find cheap flights to Southwest Side that have flexible change policies?
We know that plans can change in the blink of an eye, so booking a flexible airfare with Expedia is always a wise idea. Tick the "No change fee" box below the "Flexible change policies" filter. Your affordable, flexible flight to Southwest Side is only a few clicks away.
What are some of the general tips for travelers to Southwest Side during the COVID-19 outbreak?
In the face of COVID-19, traveling now comes with a few extra challenges. Keep in mind these worthwhile tips before boarding your plane to Southwest Side:
  • Understand what rules and restrictions apply to both your origin and destination. It may not be possible to travel depending on local circumstances, so remember to check before you book your flight.
  • When you go through airport checkpoints, keep your face mask on. You will be asked to briefly lower it for identification purposes. Travelers who refuse to wear a face mask may face civil penalties and may also be denied boarding.
  • Instead of handing a TSA officer your boarding pass, place it directly on the reader yourself. When that's done, hold it up for inspection.
  • One container of liquid hand sanitizer is now permitted in your carry-on baggage. It must be no bigger than 12 oz (350 ml), and you'll have to take it out of your bag at the X-ray machine for screening.
  • Put any personal items (phone, wallet and keys for example) in your carry-on rather than a bin to minimize handling during the screening process.
  • If you want to take food on board, put it in a clear plastic bag and then into a screening bin. This reduces the likelihood that a TSA officer will need to touch your carry-on bag or food container for inspection.

Which airlines fly to Southwest Side?
American Airlines operates flights into or near Southwest Side, including 13307 that touch down at O'Hare Intl. Airport (ORD) each month. Work out your vacation dates and then lock in your ticket early for the biggest bargain.
How can I find cheap tickets to Southwest Side?
You'll always walk away with a fabulous deal with Expedia, but our "flexible dates" search function makes it that much easier. Enter your preferred flight date, then click on the flexible dates link above to see a list of prices for nearby days. was the best price for a flight to Southwest Side in the last seven days.
How much is a flight to Southwest Side?
There were plenty of low-cost fares up for grabs in the last seven days, with the cost of a return ticket to Southwest Side varying between and . Many lucky vacationers purchased one-way seats from () for just .
What are the most popular airports to fly into in Southwest Side?
The main entryway to Southwest Side, roughly 33491 flights service O'Hare Intl. Airport (ORD) each month. Look for a top deal, reserve your fare and get set to soak up the best of this renowned region.
When is the cheapest time to fly to Southwest Side?
If you're not set on what day you jet off to Southwest Side, try to fly out earlier in the week. The cheapest day to take off is normally Tuesday, closely followed by Monday. Saturday is typically the priciest day, with lots of vacationers choosing to fly on the weekend.
How much is a plane ticket to Southwest Side?
In the last seven days, flights to Southwest Side varied between and . Prices generally depend on the departure time, airline, cabin class and when the fare is booked.
Which airlines with flights to Southwest Side employ COVID-19 cleanliness policies?
As people begin traveling again, most commercial airlines have implemented physical distancing and other vital actions to reduce the impact of COVID-19. These carriers are among them:
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.

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