---
title: "Rolla to Chicago cheap flights (RLA to ORD) - Expedia"
description: "Cheap Flights from Rolla (RLA) to Chicago (ORD) start at for one-way and for round trip. Earn your airline miles on top of our rewards!"
canonical: "https://www.expedia.com/lp/flights/rla/ord/rolla-to-chicago"
language: en-US
market: US
currency: USD
prices_as_of: 2026-11-15T18:10:55Z
---

# Cheap Flights from Rolla (RLA) to Chicago (ORD)
![A spacious airport terminal with high ceilings, check-in counters, and a Starbucks coffee shop.](https://images.trvl-media.com/place/4477519/cc6a7387-1e55-4f8e-ba5c-f5a71df2aef3.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by by O'Hare Intl Airport

## Popular airlines from Rolla, MO (RLA-Rolla National) to Chicago O'Hare Intl. Airport (ORD)

[American Airlines](https://www.expedia.com/Flights-Search?leg1=from:RLA,to:ORD,departure:11/29/2026TANYT&leg2=from:ORD,to:RLA,departure:12/6/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}])

[United](https://www.expedia.com/Flights-Search?leg1=from:RLA,to:ORD,departure:11/29/2026TANYT&leg2=from:ORD,to:RLA,departure:12/6/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}])

[Southwest Airlines](https://www.expedia.com/Flights-Search?leg1=from:RLA,to:ORD,departure:11/29/2026TANYT&leg2=from:ORD,to:RLA,departure:12/6/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}])

Southwest Airl · ines

[Delta](https://www.expedia.com/Flights-Search?leg1=from:RLA,to:ORD,departure:11/29/2026TANYT&leg2=from:ORD,to:RLA,departure:12/6/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}])

[Frontier Airlines](https://www.expedia.com/Flights-Search?leg1=from:RLA,to:ORD,departure:11/29/2026TANYT&leg2=from:ORD,to:RLA,departure:12/6/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}])

[JetBlue Airways](https://www.expedia.com/Flights-Search?leg1=from:RLA,to:ORD,departure:11/29/2026TANYT&leg2=from:ORD,to:RLA,departure:12/6/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"B6"}}])

[Alaska Airlines](https://www.expedia.com/Flights-Search?leg1=from:RLA,to:ORD,departure:11/29/2026TANYT&leg2=from:ORD,to:RLA,departure:12/6/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}])

### Be in the know
Get alerts if flight prices drop or rise\*

### Book smarter
Save up to 30% on select hotels after you book a flight\*

### Earn twice
Earn your airline miles on top of our OneKeyCash
[Learn about One Key](https://www.expedia.com/welcome-one-key)

Find the cheapest flights on Expedia from (RLA) to (ORD). Flight ticket prices change frequently based on availability and demand. We send price‑drop alerts to make air travel simple and flexible. The lowest one-way fare found on Expedia for this route in the past 7 days starts at for travel on .

## Book with confidence

### Rolla to Chicago Flights

#### The cheapest times to fly from Rolla to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Rolla to Chicago are during the month of . You can find some of the cheapest flights from Rolla to Chicago with Expedia's search tool and vast selection of airlines.

#### The best time to book a flight from Rolla to Chicago

Sunday is one of the best days to book for cheap flights from Rolla to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

#### How to find cheap round-trip tickets from Rolla to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Rolla to Chicago in 2026\. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference\*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Rolla to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

You could also save big by booking one of Expedia's [vacation packages](https://www.expedia.com/package-deals). Bundling together your Rolla to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

*\*Terms apply.*

*Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023\. The percentages you see are averages.*

## Frequently Asked Questions

### How much does a flight from Rolla, MO (RLA-Rolla National) to Chicago, IL (ORD-O'Hare Intl.) cost?

You can find cheap one-way flights and cheap return flights RLA to ORD with Expedia. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see our cheapest fares first, and use the Price Tracking tool to receive alerts when RLA to ORD ticket fares go up or down.

### What is the cheapest month to fly from Rolla, MO (RLA-Rolla National) to Chicago, IL (ORD-O'Hare Intl.)?

The cheapest month to fly from RLA to ORD is when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.

### Which airlines fly direct from Rolla, MO (RLA-Rolla National) to Chicago, IL (ORD-O'Hare Intl.)?

Enter RLA to ORD and your travel dates, then apply the 'Nonstop' filter to see only direct flights.

### How do I find cheap flights from Rolla, MO (RLA-Rolla National) to Chicago, IL (ORD-O'Hare Intl.)?

To find a cheap flight from Rolla, MO (RLA-Rolla National) to Chicago, IL (ORD-O'Hare Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up [Price Tracking](https://www.expedia.com/why/price-tracking) and receive alerts when fares go up or down.

### What is the best time to fly from Rolla, MO (RLA-Rolla National) to Chicago, IL (ORD-O'Hare Intl.)?

The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.

### What is the earliest flight from Rolla, MO (RLA-Rolla National) to Chicago, IL (ORD-O'Hare Intl.)?

Sort flights by "Departure (earliest)" on Expedia to find the earliest flight from RLA to ORD. To compare more early flights, use the "Early Morning" and "Morning" filters in your search.

### Can you fly business or first class from Rolla, MO (RLA-Rolla National) to Chicago, IL (ORD-O'Hare Intl.)?

Select the "Business class" and "First class" filters when looking for RLA to ORD flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.

### How do I earn miles on a Rolla, MO (RLA-Rolla National) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?

It's easy to earn miles on a Rolla, MO (RLA-Rolla National) to Chicago, IL (ORD-O'Hare Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of [One Key™](https://www.expedia.com/welcome-one-key), you can also earn OneKeyCash™\* on top of your airline miles when you book with Expedia.

\*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

### Is it cheaper to buy a plane ticket from Rolla, MO (RLA-Rolla National) to Chicago, IL (ORD-O'Hare Intl.) at the last minute?

Typically, booking a last minute flight from Rolla, MO (RLA-Rolla National) to Chicago, IL (ORD-O'Hare Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.

### Is it cheaper to book a Rolla, MO (RLA-Rolla National) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package?

Securing a Rolla, MO (RLA-Rolla National) to Chicago, IL (ORD-O'Hare Intl.) [Chicago Vacation Packages](https://www.expedia.com/chicago.d178248.destination-travel-guides) is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.

### Can I cancel or change the date of my flight from Rolla, MO (RLA-Rolla National) to Chicago, IL (ORD-O'Hare Intl.)?

If you booked your Rolla, MO (RLA-Rolla National) to Chicago, IL (ORD-O'Hare Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in [your itinerary](https://www.expedia.com/trips) or confirmation email. Or, head to our [Customer Service portal](https://www.expedia.com/helpcenter/) if you'd like more information.

## Travel information

| Origin airport      | Rolla, MO                    |
| ------------------- | ---------------------------- |
| Destination airport | Chicago O'Hare Intl. Airport |
| Distance            | 335 miles away               |

## Explore a world of travel with Expedia

- [Flights](?equalTargetTab=tab-0)
- [Flights from Denver (DEN) to Chicago (ORD)](https://www.expedia.com/lp/flights/den/ord/denver-to-chicago)
- [Flights from Pittsburgh (PIT) to Chicago (ORD)](https://www.expedia.com/lp/flights/pit/ord/pittsburgh-to-chicago)
- [Flights from Mumbai (BOM) to Chicago (ORD)](https://www.expedia.com/lp/flights/bom/ord/mumbai-to-chicago)
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- [Flights from Detroit (DTW) to Chicago (ORD)](https://www.expedia.com/lp/flights/dtw/ord/detroit-to-chicago)
- [Flights from El Paso (ELP) to Chicago (ORD)](https://www.expedia.com/lp/flights/elp/ord/el-paso-to-chicago)
- [Flights from Harrisburg (MDT) to Chicago (ORD)](https://www.expedia.com/lp/flights/mdt/ord/harrisburg-to-chicago)
- [Flights from Springfield (SGF) to Chicago (ORD)](https://www.expedia.com/lp/flights/sgf/ord/springfield-to-chicago)
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- [Flights from Houston (HOU) to Chicago (ORD)](https://www.expedia.com/lp/flights/hou/ord/houston-to-chicago)
- [Flights from Richmond (RIC) to Chicago (ORD)](https://www.expedia.com/lp/flights/ric/ord/richmond-to-chicago)
- [Flights from Rome (FCO) to Chicago (ORD)](https://www.expedia.com/lp/flights/fco/ord/rome-to-chicago)
- [Flights from Hyderabad (HYD) to Chicago (ORD)](https://www.expedia.com/lp/flights/hyd/ord/hyderabad-to-chicago)
- [Flights from Fort Lauderdale (FLL) to Chicago (ORD)](https://www.expedia.com/lp/flights/fll/ord/fort-lauderdale-to-chicago)
- [Flights from Cincinnati (CVG) to Chicago (ORD)](https://www.expedia.com/lp/flights/cvg/ord/cincinnati-to-chicago)
- [Flights from Sacramento (SMF) to Chicago (ORD)](https://www.expedia.com/lp/flights/smf/ord/sacramento-to-chicago)
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- [Flights from Milwaukee (MKE) to Chicago (ORD)](https://www.expedia.com/lp/flights/mke/ord/milwaukee-to-chicago)
- [Flights from Fayetteville (XNA) to Chicago (ORD)](https://www.expedia.com/lp/flights/xna/ord/fayetteville-to-chicago)
- [Flights from Delhi (DEL) to Chicago (ORD)](https://www.expedia.com/lp/flights/del/ord/delhi-to-chicago)
- [Flights from Boise (BOI) to Chicago (ORD)](https://www.expedia.com/lp/flights/boi/ord/boise-to-chicago)
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- [Flights from Salt Lake City (SLC) to Chicago (ORD)](https://www.expedia.com/lp/flights/slc/ord/salt-lake-city-to-chicago)
- [Flights from Omaha (OMA) to Chicago (ORD)](https://www.expedia.com/lp/flights/oma/ord/omaha-to-chicago)
- [Flights from Amman (AMM) to Chicago (ORD)](https://www.expedia.com/lp/flights/amm/ord/amman-to-chicago)
- [Flights from Memphis (MEM) to Chicago (ORD)](https://www.expedia.com/lp/flights/mem/ord/memphis-to-chicago)
- [Flights from Pensacola (PNS) to Chicago (ORD)](https://www.expedia.com/lp/flights/pns/ord/pensacola-to-chicago)
- [Flights from Little Rock (LIT) to Chicago (ORD)](https://www.expedia.com/lp/flights/lit/ord/little-rock-to-chicago)
- [Flights from Grand Rapids (GRR) to Chicago (ORD)](https://www.expedia.com/lp/flights/grr/ord/grand-rapids-to-chicago)
- [Flights from Greensboro (GSO) to Chicago (ORD)](https://www.expedia.com/lp/flights/gso/ord/greensboro-to-chicago)
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- [Flights from Albany (ALB) to Chicago (ORD)](https://www.expedia.com/lp/flights/alb/ord/albany-to-chicago)
- [Flights from Syracuse (SYR) to Chicago (ORD)](https://www.expedia.com/lp/flights/syr/ord/syracuse-to-chicago)
- [Flights from Philadelphia (PHL) to Chicago (ORD)](https://www.expedia.com/lp/flights/phl/ord/philadelphia-to-chicago)
- [Flights from Las Vegas (LAS) to Chicago (ORD)](https://www.expedia.com/lp/flights/las/ord/las-vegas-to-chicago)
- [Flights from Louisville (SDF) to Chicago (ORD)](https://www.expedia.com/lp/flights/sdf/ord/louisville-to-chicago)
- [Flights from Seattle (SEA) to Chicago (ORD)](https://www.expedia.com/lp/flights/sea/ord/seattle-to-chicago)
- [Flights from Birmingham (BHM) to Chicago (ORD)](https://www.expedia.com/lp/flights/bhm/ord/birmingham-to-chicago)
- [Flights from Greenville (GSP) to Chicago (ORD)](https://www.expedia.com/lp/flights/gsp/ord/greenville-to-chicago)
- [Flights from Boston (BOS) to Chicago (ORD)](https://www.expedia.com/lp/flights/bos/ord/boston-to-chicago)
- [Flights from New York (JFK) to Chicago (ORD)](https://www.expedia.com/lp/flights/jfk/ord/new-york-to-chicago)
- [Flights from Mexico City (MEX) to Chicago (ORD)](https://www.expedia.com/lp/flights/mex/ord/mexico-city-to-chicago)
- [Flights from Tucson (TUS) to Chicago (ORD)](https://www.expedia.com/lp/flights/tus/ord/tucson-to-chicago)
- [Flights from Jacksonville (JAX) to Chicago (ORD)](https://www.expedia.com/lp/flights/jax/ord/jacksonville-to-chicago)
- [Flights from Ontario Intl. Airport (ONT) to Chicago (ORD)](https://www.expedia.com/lp/flights/ont/ord/ontario-to-chicago)
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- [Flights from Buffalo (BUF) to Chicago (ORD)](https://www.expedia.com/lp/flights/buf/ord/buffalo-to-chicago)
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- [Flights from Rochester (ROC) to Chicago (ORD)](https://www.expedia.com/lp/flights/roc/ord/rochester-to-chicago)
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- [Flights from Honolulu (HNL) to Chicago (ORD)](https://www.expedia.com/lp/flights/hnl/ord/honolulu-to-chicago)
- [Flights from White Plains (HPN) to Chicago (ORD)](https://www.expedia.com/lp/flights/hpn/ord/white-plains-to-chicago)
- [Flights from Indianapolis (IND) to Chicago (ORD)](https://www.expedia.com/lp/flights/ind/ord/indianapolis-to-chicago)
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- [Flights from Minneapolis (MSP) to Chicago (ORD)](https://www.expedia.com/lp/flights/msp/ord/minneapolis-to-chicago)
- [Flights from Albuquerque (ABQ) to Chicago (ORD)](https://www.expedia.com/lp/flights/abq/ord/albuquerque-to-chicago)
- [Flights from Paris (CDG) to Chicago (ORD)](https://www.expedia.com/lp/flights/cdg/ord/paris-to-chicago)
- [Flights from Charleston (CHS) to Chicago (ORD)](https://www.expedia.com/lp/flights/chs/ord/charleston-to-chicago)
- [Flights from Washington (IAD) to Chicago (ORD)](https://www.expedia.com/lp/flights/iad/ord/washington-to-chicago)
- [Flights from Tampa (TPA) to Chicago (ORD)](https://www.expedia.com/lp/flights/tpa/ord/tampa-to-chicago)
- [Flights from Oklahoma City (OKC) to Chicago (ORD)](https://www.expedia.com/lp/flights/okc/ord/oklahoma-city-to-chicago)
- [Flights from Portland (PDX) to Chicago (ORD)](https://www.expedia.com/lp/flights/pdx/ord/portland-to-chicago)
- [Flights from Atlanta (ATL) to Chicago (ORD)](https://www.expedia.com/lp/flights/atl/ord/atlanta-to-chicago)
- [Flights from Houston (IAH) to Chicago (ORD)](https://www.expedia.com/lp/flights/iah/ord/houston-to-chicago)
- [Flights from San Diego (SAN) to Chicago (ORD)](https://www.expedia.com/lp/flights/san/ord/san-diego-to-chicago)
- [Flights from Providence (PVD) to Chicago (ORD)](https://www.expedia.com/lp/flights/pvd/ord/providence-to-chicago)
- [Flights from San Francisco (SFO) to Chicago (ORD)](https://www.expedia.com/lp/flights/sfo/ord/san-francisco-to-chicago)
- [Flights from Guadalajara (GDL) to Chicago (ORD)](https://www.expedia.com/lp/flights/gdl/ord/guadalajara-to-chicago)
- [Flights from Norfolk (ORF) to Chicago (ORD)](https://www.expedia.com/lp/flights/orf/ord/norfolk-to-chicago)
- [Flights from West Palm Beach (PBI) to Chicago (ORD)](https://www.expedia.com/lp/flights/pbi/ord/west-palm-beach-to-chicago)
- [Flights from Washington (DCA) to Chicago (ORD)](https://www.expedia.com/lp/flights/dca/ord/washington-to-chicago)
- [Flights from Miami (MIA) to Chicago (ORD)](https://www.expedia.com/lp/flights/mia/ord/miami-to-chicago)
- [Flights from St. Louis (STL) to Chicago (ORD)](https://www.expedia.com/lp/flights/stl/ord/st-louis-to-chicago)
- [Flights from Baltimore (BWI) to Chicago (ORD)](https://www.expedia.com/lp/flights/bwi/ord/baltimore-to-chicago)
- [Flights from London (LHR) to Chicago (ORD)](https://www.expedia.com/lp/flights/lhr/ord/london-to-chicago)
- [Flights from Manila (MNL) to Chicago (ORD)](https://www.expedia.com/lp/flights/mnl/ord/manila-to-chicago)
- [Flights from Savannah (SAV) to Chicago (ORD)](https://www.expedia.com/lp/flights/sav/ord/savannah-to-chicago)
- [Flights from New York (NYC) to Chicago (ORD)](https://www.expedia.com/lp/flights/nyc/ord/new-york-to-chicago)
- [Flights from Des Moines (DSM) to Chicago (ORD)](https://www.expedia.com/lp/flights/dsm/ord/des-moines-to-chicago)
- [Flights from Hartford (BDL) to Chicago (ORD)](https://www.expedia.com/lp/flights/bdl/ord/hartford-to-chicago)
- [Flights from Toronto (YYZ) to Chicago (ORD)](https://www.expedia.com/lp/flights/yyz/ord/toronto-to-chicago)
- [Flights from New York (LGA) to Chicago (ORD)](https://www.expedia.com/lp/flights/lga/ord/new-york-to-chicago)
- [Flights from San Jose (SJC) to Chicago (ORD)](https://www.expedia.com/lp/flights/sjc/ord/san-jose-to-chicago)
- [Flights from Orange County (SNA) to Chicago (ORD)](https://www.expedia.com/lp/flights/sna/ord/orange-county-to-chicago)
- [Flights from Nashville (BNA) to Chicago (ORD)](https://www.expedia.com/lp/flights/bna/ord/nashville-to-chicago)
- [Flights from Lexington (LEX) to Chicago (ORD)](https://www.expedia.com/lp/flights/lex/ord/lexington-to-chicago)
- [Flights from San Juan (SJU) to Chicago (ORD)](https://www.expedia.com/lp/flights/sju/ord/san-juan-to-chicago)

\*Available to One Key members.

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  ar: https://www.expedia.sa/lp/flights/rla/ord/rolla-to-chicago
  de-AT: https://www.expedia.at/lp/fluge/rla/ord/rolla-nach-chicago
  en-US: https://www.expedia.com/lp/flights/rla/ord/rolla-to-chicago
```