Far Southwest Side Holidays from £1,201

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Top Far Southwest Side Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was £1,633, price is now £1,201 per person
£1,201
per person
11 Jul - 18 Jul
found 18 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.4/10 Very Good! (2,277 reviews)
State of the art gym, easy access to train

Reviewed on 27 Apr 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £2,246, price is now £1,549 per person
£1,549
per person
15 Jul - 22 Jul
found 14 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (455 reviews)
Great and helpful staff very clean, a place where you don’t feel out of place

Reviewed on 25 Apr 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was £2,207, price is now £1,533 per person
£1,533
per person
4 Jun - 8 Jun
found 10 hours ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (3,280 reviews)
Really good spot and location. Staff was super helpful and nice.

Reviewed on 22 Apr 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 £2,384, price is now £1,684 per person
£1,684
per person
28 Jun - 5 Jul
found 19 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,458 reviews)
We were there for a wedding and didn't have time for much else.

Reviewed on 26 Apr 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was £2,147, price is now £1,554 per person
£1,554
per person
28 Jun - 5 Jul
found 19 hours ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (463 reviews)
I was blown away by our room. So big, clean. Also the 8th floor amenities were amazing! Will definitely be back! Everything about this place was incredible and so clean!

Reviewed on 26 Apr 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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Beverly

Beverly is well liked for its restaurants and churches. If you're hoping to see more of the larger area, Martin Luther King Drive and Jones Convocation Center are some interesting sights nearby to check out.

Find hotels in Beverly

Far Southwest Side Essential Information

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

Top hotels in Far Southwest Side

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is £98 per night from 28 Apr to 29 Apr
£98
28 Apr - 29 Apr
includes taxes & fees
8.2/10 Very Good! (2,647 reviews)
great location. clean. convenient

Reviewed on 27 Apr 2026

Hotel Felix River North/Magnificent Mile
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is £104 per night from 25 May to 26 May
£104
25 May - 26 May
includes taxes & fees
8.8/10 Excellent! (5,140 reviews)
Great place,staff and location we will be back again for the 3rd time

Reviewed on 27 Apr 2026

River Hotel
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street Chicago IL
Fully refundable
The price is £96 per night from 25 May to 26 May
£96
25 May - 26 May
includes taxes & fees
8.8/10 Excellent! (3,465 reviews)
I was only in town for one day. But it was an easy seamless check-in. The room was clean and bathroom was clean. Everything in the room work and I had no need to call or any assistance. The checkout was very simple was done on my phone as I walk down the hallway before leaving.

Reviewed on 26 Apr 2026

Club Quarters Hotel, Central Loop, Chicago
See all 4,787 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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All Inclusive Holidays
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Family Friendly Holidays

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
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

4.5/5(14 reviews)

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue

What to do in Far Southwest Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

£32
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

£29
per adult
94% of travellers recommend
Art Institute of Chicago
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.