Cheap flights To Rush Street (CHI) from $29

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Cheap Flights to Rush Street from $29 One Way, $57 Round Trip

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

Tue, Apr 21 - Wed, Apr 29
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$57 Roundtrip, found 1 hour ago
$57
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Apr 21 from Newark Liberty Intl. Airport to Midway Intl., returning Wed, Apr 29, priced at $57 found 1 hour ago
Tue, May 5 - Thu, May 7
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$58 Roundtrip, found 3 days ago
$58
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, May 5 from Dallas-Fort Worth Intl. to Midway Intl., returning Thu, May 7, priced at $58 found 3 days ago
Wed, Apr 22 - Wed, Apr 29
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$73 Roundtrip, found 2 hours ago
$73
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Apr 22 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Apr 29, priced at $73 found 2 hours ago
Wed, Apr 22 - Wed, Apr 29
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$73 Roundtrip, found 2 hours ago
$73
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Wed, Apr 22 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Apr 29, priced at $73 found 2 hours ago
Wed, Apr 22 - Wed, Apr 29
LGA
LaGuardia
ORD
O'Hare Intl.
$89 Roundtrip, found 17 hours ago
$89
Roundtrip
found 17 hours ago
Select Spirit Airlines flight, departing Wed, Apr 22 from LaGuardia to O'Hare Intl., returning Wed, Apr 29, priced at $89 found 17 hours ago
Thu, Apr 16 - Sat, Apr 18
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$97 Roundtrip, found 2 hours ago
$97
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Thu, Apr 16 from Newark Liberty Intl. Airport to O'Hare Intl., returning Sat, Apr 18, priced at $97 found 2 hours ago
Wed, Apr 29 - Wed, Apr 29
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$160 Roundtrip, found 3 days ago
$160
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Wed, Apr 29 from John F. Kennedy Intl. to O'Hare Intl., returning Wed, Apr 29, priced at $160 found 3 days ago
Sat, Apr 11 - Wed, Apr 15
LGA
LaGuardia
MDW
Midway Intl.
$160 Roundtrip, found 5 days ago
$160
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Apr 11 from LaGuardia to Midway Intl., returning Wed, Apr 15, priced at $160 found 5 days ago
Tue, Apr 21 - Tue, Apr 28
DAL
Love Field
ORD
O'Hare Intl.
$166 Roundtrip, found 3 days ago
$166
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Apr 21 from Love Field to O'Hare Intl., returning Tue, Apr 28, priced at $166 found 3 days ago
Sat, Apr 25 - Sat, May 2
LGA
LaGuardia
RFD
Greater Rockford
$167 Roundtrip, found 3 days ago
$167
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Apr 25 from LaGuardia to Greater Rockford, returning Sat, May 2, priced at $167 found 3 days ago

Rush Street Flight Information

Traveling To
Rush Street
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Frontier Airlines, Spirit Airlines, American Airlines, JetBlue Airways, Southwest Airlines
Flight Price
$57
Earliest Departing Flight
Latest Departing Flight

Book Your Flight & Hotel Together & Save

Rush Street 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

May 12 - May 15

3 night stay

Dallas (DAL) to Chicago (ORD)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $790, price is now $525 per person
$525
per person
found 18 hours ago
Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

Apr 30 - May 3

3 night stay

Dallas (DFW) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $813, price is now $593 per person
$593
per person
found 1 day ago
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Rush Street first class flight packages

Price found within the past 48 hours. Click for updated prices.
Chicago Marriott Midway
3.5-star property

Chicago Marriott Midway

8.4/10 Very Good! (924 reviews)

May 14 - May 17

3 night stay

Minneapolis (MSP) to Chicago (ORD)

Delta • Roundtrip • FirstClass
Price was $977, price is now $876 per person
$876
per person
found 1 day ago
The health club was excellent. I didn't like the Internet service at 9.95 daily.

Reviewed on Aug 20, 2025

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0-star property

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

8.2/10 Very Good! (2,828 reviews)

May 14 - May 17

3 night stay

Minneapolis (MSP) to Chicago (ORD)

Delta • Roundtrip • FirstClass
Price was $1,466, price is now $1,283 per person
$1,283
per person
found 1 day ago
Friendly helpful staff.

Reviewed on Jan 5, 2026

DoubleTree by Hilton Chicago - Alsip
4.0-star property

DoubleTree by Hilton Chicago - Alsip

8.4/10 Very Good! (1,008 reviews)

May 14 - May 17

3 night stay

Minneapolis (MSP) to Chicago (MDW)

Delta • Roundtrip • FirstClass
Price was $1,016, price is now $914 per person
$914
per person
found 1 day ago
Staff was friendly and organized, room was clean, quiet and comfortable,

Reviewed on Nov 17, 2025

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Rush Street

Traveling to Rush Street and need a cheap flight? Orbitz has great deals on flights to Rush Street right now. Plus, we offer big discounts on hotel rooms and car rentals for a great money-saving trip.

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Orbitz takes pride in providing the best customer experience possible, and that effort doesn't end with discount flights to Rush Street or user-friendly mobile apps and web tools. Orbitz Customer Service is always ready to answer questions and help you with booking, planning, or canceling your Rush Street flights. When you need us, we’re here for you!

Frequently asked questions

How much is a flight to Rush Street?
Round-trip flights to Rush Street this week ranged between $57 and $167. If you were flying one-way from New York (EWR), you could have bagged tickets from just $29.
How to book the cheapest flight to Rush Street?
Using Orbitz, you'll find some of the most amazing flight deals around from a big range of airlines. But if you're eager to boost your chances of snapping up cheap flights to Rush Street, here are some suggestions to keep in mind:

  • Taking off from or arriving at other airports can be more cost-effective. Type in your preferred departure and arrival airports. Next, click on the 'Nearby airports' function below to see what your options are.
  • If your travel plans aren't set in concrete, click on the 'Show flexible dates' option to browse flight deals for a range of departure dates. Go with any suitable cheaper fare you find.
  • To fine tune your results, hit 'Show options.' You can search based on seating class, airlines, nonstop flights and refundable flights. You can also choose the time of day you'd like to fly under 'Sort & Filter' to the left.
  • Reserve your seat as soon as you've figured out your travel dates. While it does happen occasionally, flights rarely get cheaper as your departure date approaches.
  • Save even more on your adventure by bundling your hotel, flights and car rentals into a package deal. Your travel budget will thank you for it.
  • Don't travel during the busy season if possible. By steering clear of summer and school vacations, you can make superb savings on your airfares.

How long is a flight to Rush Street?
Flight lengths depend on where you're departing from, whether that's the East Coast, the West Coast or anywhere else. Below are three of the top routes to Rush Street and 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 Rush Street?
On average, the cheapest month to book your airfare is in January. This is followed by February and August. When seeking a cheap flight to Rush Street, make sure you're ready to book. Cheap deals pop up in an instant and don't wait around!
What day of the week is the cheapest to book a flight to Rush Street?
Get a great flight deal by booking on a Tuesday, Wednesday or Saturday. These are typically the best days of the week to land cheap seats to Rush Street.
What is the cheapest day of the week to fly to Rush Street?
According to Orbitz data from 2020, you ought to hop on a plane on a Monday to get cheap flights to Rush Street. Next most inexpensive day? Tuesday. Saturday costs the most. So, consider departing early in the week if you'd like to book a wallet-friendly fare and stretch your travel budget.
What is the cheapest month to fly to Rush Street?
If you have some flexibility with your travel plans, consider departing in August. Orbitz data shows that this is generally the best month to travel if you're looking for cheap flights to Rush Street. As you might expect, airfares increase in June and flights sell out fast.
Which airlines allow free cancellation?
If you're concerned your travel plans could change, Orbitz will help you lock in a flexible fare. All you have to do is select "Filter by flexible change policies" when searching for your flights. We'll show you all the airlines that include free cancellation within 24 hours and no change fees — in addition to our awesome low prices.
What do I need for the flight to Rush Street?
The trick to a smooth and comfortable flight is being well prepared. Listed below are a few tips that'll help get you ready for your trip:

  • Your travel documents are the most important items you'll need to have with you on your flight. To avoid any hassles at check-in time, make sure that the name on your ticket corresponds with your government-issued photo ID.
  • To keep you amused on the short hop to Rush Street, download some new tracks or stock up the audiobook library on your tablet. Food can also be a nice distraction while in the air, so maybe even bring some snacks.
  • Even if you're traveling when it's 100 degrees outside, carry a sweater on board with you. Cabins can get downright chilly.

How many direct flights are there to Rush Street?
Your next exciting adventure is one easy plane trip away, with 2,332 direct flights to Rush Street every month. Search for your ideal flight with Orbitz and pick up a fantastic deal with United Airlines, American Airlines or Delta Air Lines. Other sought-after carriers that offer nonstop services include Southwest Airlines, Spirit Airlines and Air Canada.
How do I get cheap first-class/business deals to Rush Street?
Experienced travelers have a way of finding first or business-class flights to Rush Street without the sky-high price tag. Take a leaf out of their book with these helpful hints:

  • Being flexible isn't just a yoga thing. Leave some room to move around your travel dates so you can snap up more affordable airfares when a big sale drops.
  • Low-cost airlines offer first or business-class seats at a fraction of the usual price. Skip the full-service carriers and fly with one these cheaper options.
  • Make the most of your airline's rewards program and use points to upgrade your seat. Alternatively, you can try bidding for an upgrade in an online auction if available.

What is the best time to go to Rush Street?
Travelers come from near and far to go to Rush Street in January, February and May. So if you'd love to explore this amazing destination in the busy season, this is the best time to go. As with most places in the Northern Hemisphere, summer commences June 20 in Rush Street, with average daily temperatures fluctuating between 65 ºF and 75 ºF.

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.