Cheap flights To West Side (CHI) from $44

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Cheap Flights to West Side from $44 One Way, $87 Round Trip

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, Sep 17 - Tue, Sep 23
DEN
Denver Intl.
ORD
O'Hare Intl.
$87 Roundtrip, found 6 days ago
$87
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Sep 17 from Denver Intl. to O'Hare Intl., returning Tue, Sep 23, priced at $87 found 6 days ago
Tue, Sep 9 - Wed, Sep 10
TPA
Tampa Intl.
ORD
O'Hare Intl.
$87 Roundtrip, found 1 hour ago
$87
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Tue, Sep 9 from Tampa Intl. to O'Hare Intl., returning Wed, Sep 10, priced at $87 found 1 hour ago
Wed, Sep 3 - Wed, Sep 10
LAS
Harry Reid Intl.
ORD
O'Hare Intl.
$87 Roundtrip, found 3 hours ago
$87
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Wed, Sep 3 from Harry Reid Intl. to O'Hare Intl., returning Wed, Sep 10, priced at $87 found 3 hours ago
Sat, Aug 23 - Tue, Aug 26
LAS
Harry Reid Intl.
ORD
O'Hare Intl.
$88 Roundtrip, found 16 hours ago
$88
Roundtrip
found 16 hours ago
Select Spirit Airlines flight, departing Sat, Aug 23 from Harry Reid Intl. to O'Hare Intl., returning Tue, Aug 26, priced at $88 found 16 hours ago
Thu, Oct 23 - Mon, Oct 27
DEN
Denver Intl.
MDW
Midway Intl.
$95 Roundtrip, found 6 days ago
$95
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Oct 23 from Denver Intl. to Midway Intl., returning Mon, Oct 27, priced at $95 found 6 days ago
Wed, Oct 22 - Sat, Oct 25
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$97 Roundtrip, found 2 days ago
$97
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Oct 22 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Sat, Oct 25, priced at $97 found 2 days ago
Wed, Oct 22 - Sat, Oct 25
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$97 Roundtrip, found 2 days ago
$97
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Oct 22 from Minneapolis - St. Paul Intl. to Midway Intl., returning Sat, Oct 25, priced at $97 found 2 days ago
Wed, Sep 17 - Thu, Sep 18
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$97 Roundtrip, found 1 day ago
$97
Roundtrip
found 1 day ago
Select United flight, departing Wed, Sep 17 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Thu, Sep 18, priced at $97 found 1 day ago
Thu, Sep 4 - Sat, Sep 6
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$99 Roundtrip, found 3 hours ago
$99
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Thu, Sep 4 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Sat, Sep 6, priced at $99 found 3 hours ago
Sat, Aug 23 - Mon, Aug 25
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$99 Roundtrip, found 22 hours ago
$99
Roundtrip
found 22 hours ago
Select Delta flight, departing Sat, Aug 23 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Mon, Aug 25, priced at $99 found 22 hours ago

West Side Flight Information

Traveling To
West Side
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Spirit Airlines, Delta, American Airlines, United, Southwest Airlines, Sun Country Airlines, Frontier Airlines
Flight Price
$87
Earliest Departing Flight
Latest Departing Flight

Flights Review

Mar 10, 2018

Great overall service. Smooth landing. Plane was even early.

A verified traveler
Denver to Chicago · United

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West Side economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

Sep 10 - Sep 12

2 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

Sep 26 - Sep 29

3 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
citizenM Chicago Downtown
4.0-star property

citizenM Chicago Downtown

Sep 26 - Sep 29

3 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
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West Side first class flight packages

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

Fairmont Chicago at Millennium Park

8.6/10 Excellent! (1,816 reviews)

Sep 26 - Sep 28

2 night stay

Atlanta (ATL) to Chicago (ORD)

Delta • Roundtrip • FirstClass
per person
found 1 day ago
The rooms was smelly! It is more like a 3 .5 stars hotel. Towel and bedsheet had roles.

Reviewed on Jul 30, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,659 reviews)

Sep 26 - Sep 28

2 night stay

Atlanta (ATL) to Chicago (ORD)

Delta • Roundtrip • FirstClass
per person
found 1 day ago
This is the nicest hotel that I have ever stayed at. Everything was perfect!

Reviewed on Jun 16, 2025

Park Hyatt Chicago
5.0-star property

Park Hyatt Chicago

9.6/10 Exceptional! (1,000 reviews)

Sep 26 - Sep 28

2 night stay

Atlanta (ATL) to Chicago (ORD)

Delta • Roundtrip • FirstClass
per person
found 1 day ago
From the moment you walk into their lobby at the hotel, you enter a place of calm and relaxation. We stayed in a room with the Water Tower view, and if you have that as the option, take it. It was a beautiful sight to see waking up every morning. This hotel like their other properties are in a class of their own.

Reviewed on Sep 13, 2024

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West Side

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Ports and Play

Be sure to check our cruise page for free shore excursions, onboard spending, balcony upgrades and other perks. Orbitz offers last-minute, luxury, weekend and summer cruises. You can even designate which port you want to sail from and pre-book on-shore activities. Get there on the cheap with discounts on flights to West Side and West Side flights. Get more bang for your travel buck at Orbitz.

Frequently asked questions

Which airlines fly to West Side?
Look up the deals from the 20 airlines that offer flights to West Side. Whether you're eager to get comfy in first class or save cash in economy, there'll be a seat for you. Head for O'Hare Intl. Airport (ORD) with one of these major carriers:

  • United Airlines - 612 flights to West Side per month
  • American Airlines - 339 flights to West Side per month
  • Air Canada - 190 flights to West Side per month

What is the best airport to fly to in West Side?
O'Hare Intl. Airport (ORD) is the main gateway for this unique region. Once you've walked out of the arrivals area, the possibilities are endless when it comes to discovering West Side.
How much is a flight to West Side?
Travelers from near and far nabbed return-flight deals ranging from $87 to $99 this week. Starting your journey from Tampa (TPA)? The cheapest one-way fares were just $44.
How to book the cheapest flight to West Side?
With some of the most exciting flight deals around, you can jet for less with Orbitz. The following tips and hints will help you score cheap flights to West Side — and leave you with more cash to play with:

  • Departing from or landing at nearby airports may help you save on airfares. Type in your preferred departure and arrival airports. Next, click on the 'Nearby airports' function below the form fields to explore your options.
  • Similarly, click on the 'Show flexible dates' link to view the airfares on days around your selected departure. You may be able to score cheaper flight deals if your dates are flexible.
  • Select 'Show options' to filter your search results. You can choose your preferred airline and seating class here. Under 'Sort & Filter' to the left, you can even select whether you want to fly in the morning, afternoon or evening.
  • If you've worked out your travel dates, don't drag your feet booking a flight. Fares normally become more expensive as the departure date nears.
  • Bundle your flights, hotels and car rentals into a value-for-money package deal. Save your hard-earned dollars for things you're really excited about, like discovering every corner of West Side.
  • Whenever possible, avoid flying in the busy season. Airfares surge during summer, school breaks and around other vacation times like Easter and Thanksgiving.

How long is a flight to West Side?
Naturally, flight times vary based on the destination you're traveling from. But to give you an understanding of the average duration, size up these well-known routes to West Side:

  • New York, NY (LGA-LaGuardia) to O'Hare Intl. Airport (ORD) - 2 hours and 40 minutes
  • Boston, MA (BOS-Logan Intl.) to O'Hare Intl. Airport (ORD) - 2 hours and 51 minutes
  • Washington, DC (DCA-Ronald Reagan Washington National) to O'Hare Intl. Airport (ORD) - 2 hours and 13 minutes

What is the best time to book a flight to West Side?
Catch a bargain and book your tickets to West Side in January. If you've missed this month, don't stress. February and August often have low airfares as well. Just be careful you don't snooze on a sale though — cheap flights appear and vanish in the blink of an eye!
What day of the week is the cheapest to book a flight to West Side?
Typically, Tuesdays, Wednesdays and Saturdays are the cheapest days of the week to book a flight to West Side. If you're after the best airfares, search across those days and you're likely to catch an excellent flight deal.
What is the cheapest day of the week to fly to West Side?
Consider departing early in the week if you want to get cheap flights to West Side. Orbitz data from 2020 suggests Monday is generally the most affordable day to fly out, followed by Tuesday. Saturdays were shown to have the highest ticket prices. This is probably because many travelers choose to start their vacation on a weekend.
What is the cheapest month to fly to West Side?
We won't keep you in suspense — according to Orbitz data, August is generally the most inexpensive month to fly. Perfect for those who need a weekend getaway or just a break from it all before the weather turns. The least affordable time to fly is in the middle of summer, with ticket prices peaking in June.
Which airlines allow free cancellation?
Orbitz makes it easy to find airlines offering fare flexibility. Simply click on "Filter by flexible change policies" when searching for your West Side flights and voila! We'll show you options that include free cancellation within 24 hours of booking, no change fees and of course, the very best price.
What do I need for the flight to West Side?
Flying doesn't have to be a drag. In fact it can be fun if you're well prepared! Make your trip a smooth one with these helpful tips:

  • Your travel documents are the most important items you'll need to carry on your flight. To avoid any delays at the time of check-in, make sure that the personal information on your ticket corresponds with your government-issued ID.
  • To keep you entertained on the short trip to West Side, download some new songs or stock up the audiobook library on your tablet. Food can also be a tasty distraction while in the air, so pack some light snacks.
  • No matter the weather outside (or how long the flight), plane cabins can get seriously cold. Bring a hoodie on board to keep yourself warm and cozy.

How many direct flights are there to West Side?
There are 2,332 direct flights each month to West Side. When it comes to airlines that will take you there, you've got loads of choice. United Airlines, American Airlines and Delta Air Lines are some of the most popular. Southwest Airlines, Spirit Airlines and Air Canada are some other reliable carriers offering nonstop services.
How do I get cheap first-class/business deals to West Side?
There are ways of booking first or business-class fares to West Side that won't burn a hole through your savings. Pick up a seat at the front of the plane for less with these helpful tips:

  • Flexibility is essential. By being open to different travel dates, you'll have more chances of picking up a great deal on first or business-class airfares.
  • A lot of budget airlines these days have comfortable business-class seating that doesn't cost the earth.
  • Bid for an upgrade in online auctions (if available) or upgrade through your flight loyalty scheme.

What is the best time to go to West Side?
West Side is popular in March, April and May. If you plan to head there during these months, it may be an idea to book well in advance to ensure you pick up the best deals. Like to know what the summer's like in West Side? Average daily temperatures normally float between 65 ºF and 75 ºF. Like most of the Northern Hemisphere, the summer season commences June 20 here.

Nearby

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.