Far Southwest Side Holidays from £1,204

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Top Far Southwest Side Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,793, price is now £1,204 per person
£1,204
per person
30 Jul - 4 Aug
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (2,744 reviews)
Absolutely wonderful place to stay

Reviewed on 11 Jun 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
Save 100% on your flight
Price was £2,032, price is now £1,482 per person
£1,482
per person
30 Jul - 4 Aug
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,519 reviews)
Unfortunately the elevators were out, at no fault of the staff. They were fantastic at trying to give the best service possible. The room was beautiful with a breathtaking view of the lake.

Reviewed on 10 Jun 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £2,432, price is now £1,780 per person
£1,780
per person
18 Jul - 25 Jul
found 6 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (491 reviews)
Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.

Reviewed on 22 May 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was £1,881, price is now £1,392 per person
£1,392
per person
30 Jul - 4 Aug
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,727 reviews)
We stayed in this hotel in our daughter's wedding weekend. It was wonderful, the river and city view from our 18th story room was spectacular. I recommend it to.all ages.

Reviewed on 7 Jun 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was £1,847, price is now £1,404 per person
£1,404
per person
30 Jul - 4 Aug
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,791 reviews)
Old hotel and rooms. All the outlets in our room were titled and so hard to plug things in them. The outlets near the nightstands on either sides can’t accommodate a charger because they’re stuck on the side of the nightstand between it and the side of the bed. Hairdryer so old and didn’t work. Check in was exactly at 4, they weren’t lenient when I showed up at 2:40.

Reviewed on 10 Jun 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
Default Image

Ashburn

The restaurants and churches are a few reasons travellers visit Ashburn. Though there aren't many top sights in the neighbourhood, you can visit Wintrust Sports Complex and Chicago Ridge Shopping Mall, a few notable attractions nearby.

Find hotels in Ashburn

Far Southwest Side Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)

Top hotels in Far Southwest Side

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 £121 per night from 29 Jun to 30 Jun
£121
29 Jun - 30 Jun
includes taxes & fees
8/10 Very Good! (10,248 reviews)
"Old building that could really use a remodel. I've stayed in many hotels in the loop and somehow the sound from outside penetrated much more than most. The doormen were excellent though. They were very helpful and nice."

Reviewed on 11 Jun 2026

Congress Plaza Hotel
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 £130 per night from 5 Jul to 6 Jul
£130
5 Jul - 6 Jul
includes taxes & fees
8.8/10 Excellent! (2,648 reviews)
"The shuttle was a plus!"

Reviewed on 10 Jun 2026

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

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is £142 per night from 30 Jun to 1 Jul
£142
30 Jun - 1 Jul
includes taxes & fees
7.8/10 Good! (1,558 reviews)
"The hotel was clean and the rooms were decent. Did like the fact. I didn't like the fact there is no mirrors in the whole room except for the one in the bathroom. Also for the price that they charge I feel they should have had daily housekeeping but it was only offered after a 3-day stay. I asked ..."

Reviewed on 11 Jun 2026

The Chicago Hotel Collection - Magnificent Mile
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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Popular places to visit

Wrigley Field

Wrigley Field

4.5/5(40 reviews)

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

Wrigley Field
Navy Pier

Navy Pier

4/5(127 reviews)

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

Navy Pier
Millennium Park

Millennium Park

4.5/5(147 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park

What to do in Far Southwest Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£18
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

£81
per adult
88% of travellers recommend
Chicago C3® by CityPASS®
See all activities in Far Southwest Side

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 travelling 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 travellers 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?
Organise 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 holiday 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 holiday 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 travelling 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. Flight-inclusive packages are ATOL protected.