Cheap flights To Rosemont (CHI) from $29

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Cheap Flights to Rosemont from $29 One Way, $68 Round Trip

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

Tue, Apr 21 - Tue, Apr 28
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$68 Roundtrip, found 10 hours ago
$68
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Tue, Apr 21 from Newark Liberty Intl. Airport to Midway Intl., returning Tue, Apr 28, priced at $68 found 10 hours ago
Sat, May 9 - Tue, May 12
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$86 Roundtrip, found 5 days ago
$86
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, May 9 from Dallas-Fort Worth Intl. to Midway Intl., returning Tue, May 12, priced at $86 found 5 days ago
Mon, Apr 13 - Tue, Apr 14
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$87 Roundtrip, found 5 hours ago
$87
Roundtrip
found 5 hours ago
Select Spirit Airlines flight, departing Mon, Apr 13 from Newark Liberty Intl. Airport to O'Hare Intl., returning Tue, Apr 14, priced at $87 found 5 hours ago
Tue, Apr 28 - Wed, Apr 29
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$87 Roundtrip, found 6 days ago
$87
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Tue, Apr 28 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Apr 29, priced at $87 found 6 days ago
Thu, Apr 9 - Wed, Apr 22
LGA
LaGuardia
ORD
O'Hare Intl.
$104 Roundtrip, found 5 days ago
$104
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Thu, Apr 9 from LaGuardia to O'Hare Intl., returning Wed, Apr 22, priced at $104 found 5 days ago
Mon, Mar 30 - Tue, Mar 31
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$135 Roundtrip, found 11 hours ago
$135
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Mon, Mar 30 from John F. Kennedy Intl. to O'Hare Intl., returning Tue, Mar 31, priced at $135 found 11 hours ago
Sat, Apr 18 - Tue, Apr 21
LGA
LaGuardia
MDW
Midway Intl.
$144 Roundtrip, found 2 days ago
$144
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Apr 18 from LaGuardia to Midway Intl., returning Tue, Apr 21, priced at $144 found 2 days ago
Wed, May 6 - Tue, May 12
LGA
LaGuardia
MDW
Midway Intl.
$167 Roundtrip, found 11 hours ago
$167
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Wed, May 6 from LaGuardia to Midway Intl., returning Tue, May 12, priced at $167 found 11 hours ago
Wed, May 6 - Thu, May 7
DAL
Love Field
MDW
Midway Intl.
$183 Roundtrip, found 8 hours ago
$183
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Wed, May 6 from Love Field to Midway Intl., returning Thu, May 7, priced at $183 found 8 hours ago
Wed, May 6 - Thu, May 7
DAL
Love Field
ORD
O'Hare Intl.
$193 Roundtrip, found 8 hours ago
$193
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Wed, May 6 from Love Field to O'Hare Intl., returning Thu, May 7, priced at $193 found 8 hours ago

Rosemont Flight Information

Traveling To
Rosemont
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Frontier Airlines, Spirit Airlines, Southwest Airlines
Flight Price
$68
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

Book Your Flight & Hotel Together & Save

Rosemont economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile
4.0-star property

Hotel Saint Clair- Magnificent Mile

May 1 - May 3

2 night stay

Boston (BOS) to Chicago (ORD)

United • Roundtrip • Coach
Price was $545, price is now $404 per person
$404
per person
found 1 day ago
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

Apr 22 - Apr 24

2 night stay

Boston (BOS) to Chicago (ORD)

American Airlines • Coach

Chicago (ORD) to Boston (BOS)

JetBlue Airways • Coach
Price was $579, price is now $419 per person
$419
per person
found 1 day ago
Hilton Garden Inn Chicago Downtown South Loop
3.0-star property

Hilton Garden Inn Chicago Downtown South Loop

May 12 - May 16

4 night stay

Los Angeles (LAX) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $849, price is now $630 per person
$630
per person
found 20 hours 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! (3,495 reviews)

May 7 - May 10

3 night stay

Boston (BOS) to Chicago (ORD)

JetBlue Airways • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,037, price is now $714 per person
$714
per person
found 13 hours ago
I recommend 100% Everything was good, the staff, room and the food. Also, it is located in a good area.

Reviewed on Jan 14, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0-star property

Sable at Navy Pier Chicago, Curio Collection by Hilton

9.4/10 Exceptional! (2,401 reviews)

May 7 - May 10

3 night stay

Boston (BOS) to Chicago (ORD)

JetBlue Airways • Roundtrip • PremiumEconomy
Price was $1,112, price is now $840 per person
$840
per person
found 10 hours ago
Courteous staff, clean room, conveniently located right on the pier.

Reviewed on Nov 3, 2025

Pendry Chicago
4.5-star property

Pendry Chicago

9.4/10 Exceptional! (1,140 reviews)

May 7 - May 10

3 night stay

Boston (BOS) to Chicago (ORD)

JetBlue Airways • Roundtrip • PremiumEconomy
Price was $1,102, price is now $841 per person
$841
per person
found 10 hours ago
Room was clean and comfortable. We really appreciated the chocolates and water!

Reviewed on Feb 25, 2026

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Rosemont first class flight packages

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

Hotel Felix River North/Magnificent Mile

8.2/10 Very Good! (2,582 reviews)

May 7 - May 12

5 night stay

Seattle (SEA) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,300, price is now $1,103 per person
$1,103
per person
found 1 day ago
The rooms were clean and smelled fresh.

Reviewed on Jan 8, 2026

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (3,495 reviews)

May 7 - May 12

5 night stay

Seattle (SEA) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,668, price is now $1,230 per person
$1,230
per person
found 1 day ago
I recommend 100% Everything was good, the staff, room and the food. Also, it is located in a good area.

Reviewed on Jan 14, 2026

Eurostars Magnificent Mile
4.0-star property

Eurostars Magnificent Mile

9/10 Wonderful! (3,314 reviews)

May 7 - May 12

5 night stay

Seattle (SEA) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,535, price is now $1,300 per person
$1,300
per person
found 1 day ago
In convenient area either by walking or uber

Reviewed on Oct 18, 2025

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Rosemont

Snag some “suite” deals when you add cheap hotel rooms to Rosemont flights at Orbitz. You can score tickets to ballgames, concerts and other activities while planning your low fare flights. For non-stop air tickets or planned layovers, Orbitz is your discount travel resource.

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Non-Stop or Stop and Visit

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All in One

Now you can custom design the perfect travel package with Orbitz and save more when booking your flights to Rosemont. Do you have a favorite airline, hotel or car rental company? Every page at Orbitz gives you complete freedom to create your travel plans according to your unique wants and needs. Orbitz is designed to meet your discount travel planning needs completely and conveniently.

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 $68 to $193 this past week. The best price to travel one-way was $29, coming from New York (EWR).
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.