Cheap flights To Rosemont (CHI) from $25

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Cheap Flights to Rosemont from $25 One Way, $58 Round Trip

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

Wed, Jun 24 - Tue, Jun 30
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$58 Roundtrip, found 6 days ago
$58
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Jun 24 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Jun 30, priced at $58 found 6 days ago
Wed, Aug 5 - Tue, Aug 11
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$88 Roundtrip, found 5 days ago
$88
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, Aug 5 from Dallas-Fort Worth Intl. to Midway Intl., returning Tue, Aug 11, priced at $88 found 5 days ago
Tue, Jul 7 - Tue, Jul 21
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$96 Roundtrip, found 6 days ago
$96
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Tue, Jul 7 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jul 21, priced at $96 found 6 days ago
Mon, Aug 10 - Tue, Aug 18
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$96 Roundtrip, found 7 hours ago
$96
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Mon, Aug 10 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Aug 18, priced at $96 found 7 hours ago
Thu, Aug 27 - Sat, Sep 5
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$110 Roundtrip, found 6 days ago
$110
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Aug 27 from Los Angeles Intl. to O'Hare Intl., returning Sat, Sep 5, priced at $110 found 6 days ago
Tue, Aug 25 - Wed, Aug 26
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Select United flight, departing Tue, Aug 25 from Newark Liberty Intl. Airport to O'Hare Intl., returning Wed, Aug 26, priced at $137 found 1 day ago
Wed, Aug 12 - Wed, Sep 30
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$157 Roundtrip, found 1 hour ago
$157
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Wed, Aug 12 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Sep 30, priced at $157 found 1 hour ago
Wed, Aug 12 - Wed, Sep 30
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$157 Roundtrip, found 1 hour ago
$157
Roundtrip
found 1 hour ago
Select Delta flight, departing Wed, Aug 12 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Sep 30, priced at $157 found 1 hour ago
Wed, Aug 12 - Wed, Sep 30
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$157 Roundtrip, found 1 hour ago
$157
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Wed, Aug 12 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Sep 30, priced at $157 found 1 hour ago
Wed, Aug 5 - Wed, Aug 26
DAL
Love Field
MDW
Midway Intl.
$183 Roundtrip, found 1 day ago
$183
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Aug 5 from Love Field to Midway Intl., returning Wed, Aug 26, priced at $183 found 1 day ago

Rosemont Flight Information

Traveling To
Rosemont
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Frontier Airlines, United, Southwest Airlines, Delta, American Airlines
Flight Price
$58
Earliest Departing Flight
Latest Departing Flight

Book Your Flight & Hotel Together & Save

Rosemont economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Emily Hotel
4.0-star property

The Emily Hotel

Jul 15 - Jul 18

3 night stay

Boston (BOS) to Chicago (ORD)

Delta • Roundtrip • Coach
Save 100% on your flight
Price was $994, price is now $617 per person
$617
per person
found 1 day ago
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

Jul 15 - Jul 18

3 night stay

Boston (BOS) to Chicago (ORD)

Delta • Roundtrip • Coach
Save 100% on your flight
Price was $1,062, price is now $653 per person
$653
per person
found 1 day ago
Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

Jul 15 - Jul 18

3 night stay

Boston (BOS) to Chicago (ORD)

Delta • Roundtrip • Coach
Save 100% on your flight
Price was $1,178, price is now $748 per person
$748
per person
found 1 day ago
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See all available trips from Boston to Rosemont
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Rosemont premium 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

9.4/10 Exceptional! (4,319 reviews)

Jul 17 - Jul 19

2 night stay

Dallas (DFW) to Chicago (ORD)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,055, price is now $801 per person
$801
per person
found 1 day ago
Nice staff. Clean. Great rooftop bar!! Great location. Great included breakfast buffet! I prefer a comforter rather than a sheet and blanket but still loved it!!

Reviewed on Jun 5, 2026

Level Chicago Fulton Market
4.0-star property

Level Chicago Fulton Market

9.2/10 Wonderful! (491 reviews)

Jul 27 - Jul 31

4 night stay

Dallas (DFW) to Chicago (ORD)

Frontier Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,588, price is now $1,058 per person
$1,058
per person
found 12 hours ago
Hotel Felix River North/Magnificent Mile
4.0-star property

Hotel Felix River North/Magnificent Mile

8.2/10 Very Good! (2,744 reviews)

Jul 27 - Jul 31

4 night stay

Dallas (DFW) to Chicago (ORD)

Frontier Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,237, price is now $841 per person
$841
per person
found 12 hours ago
Best vibe. In the mix!

Reviewed on May 2, 2026

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Rosemont

If you are looking for affordable flights to Rosemont, look no further. Orbitz offers discounted rates to many destinations.

Bargain flights to Rosemont now available

As you review your budget and travel plans, consider the low fares Orbitz offers on Rosemont flights. With Orbitz, booking flights to Rosemont is easy and the lowest prices are guaranteed.

Easy self-help service offered

Orbitz offers cutting edge mobile tools that allow you to review and make bookings from your Android or iPhone mobile device with a simple application. You can easily and conveniently update your information or book your trip using this service. You are also able to obtain information on affordable hotel packages and receive frequent flight updates. You will receive confirmation of bookings or reservations made using the mobile service on the same day of the request. Change details or receive updates on your Rosemont flights by visiting the Orbitz site or mobile application.

Orbitz looks after you

Orbitz ensures that you are kept informed with up-to-date flight information, providing feedback to up to six contact numbers to ensure that everyone receives the feedback. In addition to providing the discounted deals on Rosemont flights, Orbitz is also able to structure a package based on your needs for activities, car hire and accommodations.

Traveler profile updates

After booking your Rosemont flights, you may access your account profile on the Orbitz site and update your frequent flyer or loyalty membership details. This information will remain on the system and will be available for you to access when you make any future bookings with Orbitz.

Frequently asked questions

Which airlines fly to Rosemont?
With 20 airlines to pick from, finding the ideal flight that matches your budget and travel dates should be a piece of cake. O'Hare Intl. Airport (ORD) is a major entry point to Rosemont and where you're likely to be disembarking. These top international carriers are ready when you are:

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

What is the best airport to fly to in Rosemont?
O'Hare Intl. Airport (ORD), around 2 miles southwest of central Rosemont, is one choice. Midway Intl. Airport (MDW) is another port of entry to this exciting city. Compare the flight deals to both airports, as well as which terminal is closer to where you're staying.
How much is a flight to Rosemont?
If you're looking at flights back and forth, airfares ranged from $58 to $183 this past week. The best price to travel one-way was $25, coming from Dallas (DFW).
How to book the cheapest flight to Rosemont?
With Orbitz, you'll uncover some of the most affordable flight deals around from a huge range of airlines. But if you'd like to improve your chances of nabbing cheap flights to Rosemont, here are some pointers to keep in mind:

  • Depending on your departure point, choose the 'Nearby airports' function (located under the departure and arrival form fields). Occasionally, alternative departure points work out cheaper.
  • If you're flexible with your plans, click on the 'Show flexible dates' link. It'll display the flight deals for the days before and after your chosen departure. Ticket prices often vary depending on what day it is.
  • You can also use the 'Show options' link to filter results for your preferred airline, seating class, nonstop flights and refundable flights. Under 'Sort & Filter' to the left, you can even pick the time of day you'd like to fly.
  • Once you've settled on your travel dates, don't delay booking your flight. Prices generally get dearer as the departure date gets closer.
  • Combine your flights, hotels and car rental into a value-for-money package deal. Save your dollars for things you're really excited about, like exploring every corner of Rosemont.
  • Flying during the busy season can mean costly airfares. Try to plan your trip outside of popular periods, such as Easter, Thanksgiving and school breaks.

How long is a flight to Rosemont?
The United States is big, so that depends on which airport you're departing from. To make vacation planning a bit easier, we've chosen three of the main routes to Rosemont and worked out their average flight times:

  • 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 Rosemont?
Book your seats to Rosemont in January. This is the perfect time of the year for bargain airfares, followed by February and August. Snap up cheap flights and enjoy your dream vacation with Orbitz.
What day of the week is the cheapest to book a flight to Rosemont?
Make a booking on a Tuesday, Wednesday or Saturday. Generally, these are the cheapest days of the week to purchase airfares to Rosemont. The vacation of your dreams starts with an impressive flight deal!
What is the cheapest day of the week to fly to Rosemont?
Consider flying early in the week to nab cheap flights to Rosemont. Orbitz data from 2020 shows Monday is typically the most affordable day to set off, followed by Tuesday. Saturdays were shown to have the most expensive ticket fares. This is possibly because most passengers choose to start their escape on a weekend.
What is the cheapest month to fly to Rosemont?
Consider flying during August if you're sticking to a budget. Orbitz data has found that it's generally the best month for cheap flights to Rosemont. June is when prices are at their most expensive.
Which airlines allow free cancellation?
We understand that plans change and flexibility matters. That's why you can easily search for flights that have free cancellation and no change fees on Orbitz. Simply click on "Filter by flexible change policies" and we'll find you fares with more flexibility than candy in a hot car!
What do I need for the flight to Rosemont?
Flying doesn't have to be a drag. In fact it can be fun with a little pre-planning! Make your flight a comfortable one with these handy tips:

  • Whether you print it out beforehand or use an electronic one, you'll need your boarding pass to step foot on the plane. You'll also need some kind of government-issued ID. If you're flying internationally, make sure your passport is valid and you've looked into visa requirements.
  • Take some activities to keep you entertained on your trip to Rosemont. Books, magazines and devices like tablets and e-readers should do the trick. Be sure to take a bottle of water as well. Even on short flights, it's important to stay hydrated.
  • Even if you're traveling when it's 90 degrees outside, carry a sweater or cardigan on board with you. Cabins are notorious for getting a bit chilly!

How many direct flights are there to Rosemont?
With roughly 2,332 direct flights every month, you'll be heading straight into Rosemont and embarking on a fantastic new adventure in no time at all. Some of the carriers that journey nonstop to Rosemont include United Airlines, American Airlines and Delta Air Lines. Southwest Airlines, Spirit Airlines and Air Canada are some other popular options.
How do I get cheap first-class/business deals to Rosemont?
Smart travelers have a talent for finding first or business-class flights to Rosemont without the steep price tag. You can do the same with these helpful hints:

  • Flexibility is important. By being open to a variety of travel dates, you'll have better odds of picking up a rewarding deal on first or business-class airfares.
  • Search for a low-cost carrier that has seats in business class. They often come with extra space and a glass of bubbly — but at a more affordable price.
  • Take advantage of your airline's loyalty scheme and upgrade your seat. Alternatively, you can try bidding for an upgrade in online auctions.

How to get into Rosemont from the airport?
If you like the convenience of having your own set of wheels, reserve an O'Hare Intl. Airport (ORD) car rental with one of the two outlets at O'Hare Intl. Airport (ORD). Thrifty Car Rental and Dollar have some terrific rides to choose from. Once you've grabbed the keys, the center of Rosemont is around 2 miles to the northeast. Or, you might prefer to take a taxi into town and rent a vehicle from the downtown area after you've found your bearings? Rosemont car rentals always has a variety of terrific deals available.
What is the best time to go to Rosemont?
If you'd like to experience the unique vibe of Rosemont in peak season, May, June and August are the best months to visit. June 20 marks the onset of summer in the Northern Hemisphere and is a wonderful time to go if you savor the great outdoors. Around this time of the year, average daily temperatures usually range from 65 ºF to 75 ºF.
Travel tips for Rosemont

  • Allstate Arena is one of this vibrant city's best-loved attractions. Reserve a room close to the downtown area and stop by whenever you want.
  • If you'd love to venture farther afield and check out other Rosemont drawcards, collect the keys to a car rental and follow the road signs to Wrigley Field. It won't take long to get there from the hustle and bustle.
  • When you're ready to explore more amazing places in Chicago, jump back in the car and road-trip it to Homewood. One of the region's other happening cities, the possibilities for fun are endless here.

More to Explore

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.