Far Southwest Side Vacation Packages

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Top Far Southwest Side 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 $1,839, price is now CA $1,245 per person
CA $1,245
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,127 reviews)
Beautiful hotel. Very clean which is very important to me. Couldn’t have asked for a more perfect location. Food and drink prices at the restaurant/bar were high. Other than that, would highly recommend.

Reviewed on Jun 16, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $2,406, price is now CA $1,755 per person
CA $1,755
per person
Aug 1 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,327 reviews)
The staff was great. The room was nice but I would have preferred more towels. The remote in our room wasn’t working fully as well as the steamer in the room. Otherwise, it is a good hotel but would not recommend for families.

Reviewed on Jun 15, 2026

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was CA $2,235, price is now CA $1,664 per person
CA $1,664
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
Fantastic, attentive staff. Beautiful facilities.

Reviewed on Jun 17, 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 $2,401, price is now CA $1,787 per person
CA $1,787
per person
Aug 1 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (2,535 reviews)
Great location and food court in area. Great for family fun

Reviewed on Jun 17, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was CA $2,776, price is now CA $2,101 per person
CA $2,101
per person
Aug 1 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (3,735 reviews)
Excellent hotel to stay in. Surrounded by so many things Chicago has to offer. Right across from the river. We were greeted nicely, was able to upgrade to a nicer room at a fair price. Check in was smooth. Room was very nice, well maintained hotel lobby, rooms hallways etc. had breakfast in the Land and Sea restaurant downstairs due to a rainy morning. Would definitely recommend staying at the London House for a stay in Chicago.

Reviewed on Jun 15, 2026

Where to stay in Far Southwest Side

Find the best Far Southwest Side areas and neighborhoods for the activities you enjoy most. Learn more about Far Southwest Side
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Ashburn

The restaurants and churches are just a few features travelers like about Ashburn. If you want to do some sightseeing nearby, Childrens Museum of Oak Lawn and Wintrust Sports Complex are a few top places to visit.

Find hotels in Ashburn

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Far 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 $191 per night from Jun 29 to Jun 30
CA $191
CA $227 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,295 reviews)
"Have to pay for parking plus the ac barely works"

Reviewed on Jun 17, 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $223 per night from Jul 1 to Jul 2
CA $223
CA $266 total
Jul 1 - Jul 2
includes taxes & fees
7.8/10 Good! (1,587 reviews)
"Amazing! My daughter and I loved it, including the location."

Reviewed on Jun 17, 2026

The Chicago Hotel Collection - Magnificent Mile
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is CA $201 per night from Jul 3 to Jul 4
CA $201
CA $229 total
Jul 3 - Jul 4
includes taxes & fees
8.8/10 Excellent! (2,685 reviews)
"Hotel is conveniently located nearby the Chicago O’Hare airport. The room was clean and amenities were good for our stay. Shuttle from the airport to the hotel was helpful."

Reviewed on Jun 17, 2026

Hyatt Regency O'Hare Chicago
See all 4,708 properties in Far 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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Stay near popular Far Southwest Side attractions

Highland Community Bank

Learn about the local history of Chicago when you take a trip to Highland Community Bank.
See properties

Frequently asked questions

Can I cancel my flight booking to Far Southwest Side due to COVID-19?
If you've yet to book your tickets, check the terms and conditions of the airfare you're considering. If you've already reserved your flight to Far Southwest Side, make use of our Customer Service Portal. It will help determine which COVID-19 policies are applicable to your reservation and provide you with the next steps.
What's the best way to find cheap flights to Far Southwest Side that have flexible change policies?
When it comes to traveling these days, flexibility is crucial. That's why we've added a "No change fee" filter to help you locate cheap and flexible tickets to Far Southwest Side. It's near the top left of your screen directly under the "Flexible change policies" heading.
What are some of the general tips for travelers to Far Southwest Side during the COVID-19 outbreak?
COVID-19 has ushered in dramatic changes to how we travel. If you're planning an escape to Far Southwest Side, these tips will help you navigate these new rules and challenges:
  • Before you lock in a flight, check if any travel restrictions apply — in both your origin and destination. Stay informed with the latest updates by reviewing government travel advisories.
  • When you go through airport screening, keep your face mask on. You will be required to lower it briefly to verify your identity. Passengers who refuse to wear a mask may be fined and denied boarding.
  • Rather than handing a TSA agent your boarding pass, position it directly on the reader yourself. After that, hold it up for inspection.
  • TSA is now permitting passengers to take one container of hand sanitizer, up to 12 oz (350 ml) in size, in carry-on bags. This will have to be removed from your bag for scanning.
  • Place any personal items (e.g, keys, phone and wallet) in your carry-on rather than a bin to reduce handling during the screening process.
  • Separate any food you have for X-ray screening. Putting it in a clear plastic bag and into a bin reduces the need for a TSA employee to handle and inspect your belongings.

Which airlines fly to Far Southwest Side?
Organize your seat with American Airlines and then start putting together your Far Southwest Side travel itinerary. This leading carrier provides 13307 flights every month to O'Hare Intl. Airport (ORD), a main gateway.
How can I find cheap tickets to Far Southwest Side?
In the last seven days, was the lowest price for a flight to Far Southwest Side. For an even cheaper fare, book well ahead of time and be flexible with your dates. Search for your trip to Far Southwest Side, then compare prices for nearby days by clicking on the "flexible dates" link above.
How much is a flight to Far Southwest Side?
In the last seven days, round-trip airfares to Far Southwest Side sold from just and reached a maximum price of . For one-way fares taking off from (), the cheapest seat during this time was only .
What are the most popular airports to fly into in Far Southwest Side?
Start arranging your Far Southwest Side vacation by booking a fare on one of the 33491 flights each month to O'Hare Intl. Airport (ORD). This is the region's main entry point.
When is the cheapest time to fly to Far Southwest Side?
If you'd prefer to spend your vacation money enjoying the best of Far Southwest Side rather than on your flight there, jet off earlier in the week. The most affordable day to travel is normally Tuesday, with Monday a close second. With many folks traveling over the weekend, Saturday often has the highest ticket prices.
How much is a plane ticket to Far Southwest Side?
Fares to Far Southwest Side varied from to in the last seven days. Typically, the quicker you book the better the price.
Which airlines with flights to Far Southwest Side employ COVID-19 cleanliness policies?
As countries begin to open their borders, most airlines have resumed business with new measures including physical distancing and enhanced disinfection measures. Here's what different carriers are doing to ease the spread of COVID-19:
  • 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.