Far Southwest Side Vacations from ￥357,749

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The Latest Far Southwest Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Orrington / Evanston

Hilton Orrington / Evanston

4 out of 5
Downtown Evanston
Price was ￥452,878, price is now ￥357,749 per person
￥357,749
per person
May 29 - Jun 3
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
7.6/10 Good! (758 reviews)
Nice dinning spot, great service

Reviewed on Mar 30, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was ￥716,628, price is now ￥518,857 per person
￥518,857
per person
May 29 - Jun 3
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (902 reviews)
The check in process was a little crazy, can’t say I have ever needed a background check to stay somewhere so it was a bit time consuming although I suppose good to know safety is a priority. View from property was the best part hands down! Cost of overall stay was great deal, parking for $65 a night was a bit disappointing because it is nice to have it on site. Overall would stay again.

Reviewed on Apr 14, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was ￥711,740, price is now ￥515,764 per person
￥515,764
per person
May 29 - Jun 3
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
The staff was the best part of the hotel, accommodating, polite and patient. Rooms were so so but they offer so many amenities that is more than makes up for it

Reviewed on Apr 14, 2026

Ohio House Motel

Ohio House Motel

3 out of 5
Downtown Chicago
Price was ￥546,284, price is now ￥416,107 per person
￥416,107
per person
May 29 - Jun 3
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,090 reviews)
Great location. Friendly staff. Loud city.

Reviewed on Apr 12, 2026

Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton

4 out of 5
Downtown Chicago
Price was ￥543,638, price is now ￥431,376 per person
￥431,376
per person
May 29 - Jun 3
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,520 reviews)
This is our favorite hotel in Chicago. The only thing that was different on our last trip was the parking garage next door. It is under new ownership, and they made it very difficult to leave and come back, even though we bought a three-day pass with in-and-out privileges. The management at Claridge House is aware of the situation and is working on a solution.

Reviewed on Apr 12, 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

The restaurants and churches are just a few features travelers like about Beverly. If you want to do some sightseeing nearby, Chicago State University and Jones Convocation Center are a few top places to visit.

Find hotels in Beverly

Find the Best Far Southwest Side Vacation Packages

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 ￥19,650 per night from Apr 26 to Apr 27
￥19,650
￥23,068 total
Apr 26 - Apr 27
includes taxes & fees
8/10 Very Good! (10,142 reviews)
My friend was given a very small room and never got room service. Also, we want adjoining rooms, which they could not give us but put us on the same floor as far apart as was possible. I had requested the adjoining rooms with Expedia long before we arrived. Obviously, you have no clout with them. ...

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 ￥21,966 per night from Apr 26 to Apr 27
￥21,966
￥25,787 total
Apr 26 - Apr 27
includes taxes & fees
9/10 Wonderful! (4,130 reviews)
Accommodated my early check-in, super easy check-in, and I was afraid there wasn’t gonna be air-conditioning from other reviews, but there was in fact air conditioning in my room and it was icy cold just how I like it 10 out of 10 stay

Reviewed on Apr 14, 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 ￥24,699 per night from Apr 28 to Apr 29
￥24,699
￥28,995 total
Apr 28 - Apr 29
includes taxes & fees
8.6/10 Excellent! (5,857 reviews)
Clean, friendly staffs, good service. Love happy hours with drinks and appetizers, breakfast service is awesome.

Reviewed on Apr 13, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,804 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.

Discover the most popular places to visit in Far Southwest Side

Wrigley Field

Wrigley Field

4.5/5(2,149 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(461 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(4,923 reviews)

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

Navy Pier

What to do in Far Southwest Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥4,285
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

￥6,982
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

￥6,348
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 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.