How Do I Find Cheap Flights to Chicago in 2026?
To find cheap flights to Chicago in the US in 2026, price both O'Hare and Midway with flexible dates, compare the same flights on Expedia, Priceline and Trip.com, use the 24-hour hold or cancel rule, count the ride into town, and go through ShopBack US before you book. The same method works for Denver, San Diego, New Orleans and Nashville.
ShopBack US is a free Cashback app and website. You start from a booking site's page on ShopBack, book your flight on that site as usual, and part of what you paid comes back to you as cash you can withdraw. Join ShopBack US for free before you start searching.
Flight and hotel booking sites on ShopBack US include Trip.com, Expedia, Priceline, CheapOair, Booking.com, Hotels.com and Agoda. The same method in this guide also works for Denver, San Diego, New Orleans and Nashville, and each city has its own section below.
How do I find cheap flights to Chicago?
Price O'Hare and Midway side by side, search a range of dates, and compare the same flights on two or three sites before you book. Chicago is one of the few US cities where the airport you pick can change the fare, so treat the two airports as one search.
According to Choose Chicago, the city's official tourism body, O'Hare International Airport (ORD) is about 17 miles from downtown, offers more than 1,000 direct daily flights and has more runways than any other commercial airport in the country. Midway International Airport (MDW) is about 10 miles from downtown and is connected to it by public transportation.
The CTA runs trains from both. According to the CTA, the Blue Line from O'Hare to downtown takes about 40 to 45 minutes, and the Orange Line from Midway to the Loop takes about 20 to 25 minutes. That matters, because a cheap fare is only cheap if the ride into town is too.
A booking routine that usually works for Chicago:
- Search ORD and MDW together and note which airlines fly each from your home airport.
- Use the calendar view and look at the week either side of your ideal day.
- Compare like for like, with bags and seats added, on Expedia, Priceline or Trip.com, then the airline's own site.
- Hold the fare with the 24-hour rule (below) while you keep watching.
- Go through ShopBack before you book, then book.
Flights to Chicago in 2026: rules and changes that help
Two things work in your favor in 2026: the federal 24-hour rule and a wider choice of fares on booking sites.
The 24-hour rule. Under federal regulation (14 CFR 259.5), covered airlines must let you hold a reservation at the quoted fare without payment, or cancel it without penalty, for at least 24 hours after booking, if you book one week or more before departure. Each airline chooses which of the two it offers and has to state it on the last page of its booking process. If you book through a booking site, that site's own cancellation terms also apply, so read them before you pay.
Southwest fares on Priceline. According to Priceline, Southwest Airlines fares have been bookable on Priceline since August 6, 2025, with all Southwest fare types available so you can compare fare bundles side by side. Priceline says Southwest runs more than 4,000 daily flights to over 100 destinations. For Chicago that widens the comparison, especially if you are open to Midway.
How do I find cheap flights to Denver?
For Denver, the saving comes from timing and comparison, because nearly every traveler lands at one airport, Denver International (DEN). Search a range of dates, compare the same flights and bags on two or three booking sites, and hold a good fare with the 24-hour rule.
Getting into the city is straightforward. According to Denver Union Station, the RTD A Line runs between Union Station and DEN in about 37 minutes, and an Airport Day Pass costs $10 at the time of writing, valid for unlimited RTD rides that service day. The A Line runs every 15 minutes from about 6 AM to 8 PM and every 30 minutes in the early morning and late evening.
Since Southwest fares are now on Priceline, one Priceline search compares them with other airlines, and bag and seat fees often decide which Denver fare is really cheapest.
How do I find cheap flights to San Diego?
Compare the same flights into San Diego International Airport (SAN) on two or three booking sites, include Southwest, and keep your dates flexible. According to SAN, it is the busiest single-runway airport in the United States, it sits on 661 acres about 3 miles northwest of downtown, and its largest carrier is Southwest Airlines, followed by American, United, Delta and Alaska.
Because Southwest is the biggest airline at SAN and Priceline now sells Southwest fares, a Priceline search is a useful second check alongside Expedia or Trip.com.
The short distance keeps ground costs low. According to SAN, MTS Route 992 stops at Terminals 1 and 2 and runs every day from 4:15 a.m. to midnight, every 15 minutes, with connections to the Trolley, COASTER and Amtrak.
How do I find cheap flights to New Orleans?
Pick dates away from the city's biggest festival weekends if you can, then compare the same flights into Louis Armstrong New Orleans International Airport (MSY) on two or three booking sites. New Orleans has a packed event calendar: New Orleans and Company, the city's official tourism body, counts more than 130 festivals and celebrations a year, with Mardi Gras the best known. Flights and hotels usually price higher around the big ones.
According to New Orleans and Company:
- 15 airlines fly nonstop to New Orleans, from about 50 destinations, including five international ones.
- Frequency varies by city, from once a week to several flights a day, and some routes are seasonal.
- The RTA 202 Airport Express bus runs from the airport to downtown for a $1.25 fare at the time of writing.
- Taxis charge $36 each way for one or two people from the airport to the central business district and French Quarter, with $14 each for three or more and a $1 bag fee, at the time of writing.
How do I find cheap flights to Nashville?
Search Nashville International Airport (BNA) with flexible dates, compare the identical flights and bags on two or three booking sites, and use the 24-hour rule to hold a fare. Nashville is a popular weekend city, so midweek trips often price lower than Friday to Sunday ones.
Getting downtown is cheap. According to WeGo Public Transit, Route 18 runs between BNA and the Elizabeth Duff Transit Center at WeGo Central downtown for $2 each way at the time of writing. Express trips take about 20 minutes and local trips 35 to 45 minutes, depending on traffic.
Chicago, Denver, San Diego, New Orleans and Nashville at a glance
| City | Main airport(s) | Getting downtown | Search tip |
|---|---|---|---|
| Chicago | O'Hare (ORD), Midway (MDW) | CTA Blue Line from ORD, about 40 to 45 min; Orange Line from MDW, about 20 to 25 min | Price both airports together |
| Denver | Denver International (DEN) | RTD A Line, about 37 min; $10 Airport Day Pass | Compare dates and bags |
| San Diego | San Diego International (SAN) | MTS Route 992, every 15 min; airport about 3 miles from downtown | Include Southwest |
| New Orleans | Louis Armstrong (MSY) | RTA 202 Airport Express, $1.25 fare | Avoid big festival weekends |
| Nashville | Nashville International (BNA) | WeGo Route 18, $2, express about 20 min | Fly midweek |
Cheapest month for flights to Chicago and the other four cities
There is no fixed cheapest month, because fares change daily with demand, events and airline schedules. The dependable way to find the cheapest month for your own route is the month or calendar view on a booking site, which shows the lowest fare for each day.
Fares usually rise around holidays, school breaks and big events such as Mardi Gras in New Orleans or a major convention in Chicago, and on weekends in leisure cities such as Nashville. Midweek trips, booking ahead and a price alert on your route usually help. For timing advice by route type and season, see when to book flights.
Flights to Chicago: best deals in the US in 2026
The best flight deals usually show up during booking-site sales around Black Friday (27 November 2026), Cyber Monday (30 November 2026) and Travel Tuesday (1 December 2026), and through each site's own deal formats. Check each booking site's deals page in early November.
Flight and hotel packages on Expedia and Priceline can cost less than booking each part separately, so price both ways. Whatever the deal, go through ShopBack before you book.
Expedia vs Priceline for flights to Chicago in 2026
Neither Expedia nor Priceline is cheaper every time. Both search many airlines, so the same flight is often priced close on both. The differences are in the programs and deal formats around the booking.
| Expedia | Priceline | |
|---|---|---|
| Rewards | One Key, shared with Hotels.com and Vrbo | Priceline VIP; Southwest bookings also earn Rapid Rewards, according to Priceline |
| Deal formats | Flight and hotel packages | Express Deals, packages, sale events |
| Good fit if | You also book stays on Expedia, Hotels.com or Vrbo | You fly Southwest or like Express Deals |
| ShopBack step | Open Expedia on ShopBack, then tap through | Open Priceline on ShopBack, then tap through |
For more on getting the most from Expedia, see how to save on Expedia.
Expedia, Priceline, CheapOair and Trip.com for US flights
All four compare many airlines at once; beyond Expedia and Priceline above, two more are worth a check.
- CheapOair. Run by Fareportal, a New York-based travel company. According to Fareportal, CheapOair offers flights on over 500 airlines, and Fareportal offers live customer support 24/7.
- Trip.com. A good place to compare fares on the same route. Book through ShopBack without a code. More detail is in our Trip.com guide.
Go through ShopBack before you book
Booking a trip online: pick your dates, compare flights and hotels, go through ShopBack to the booking site, then pay with a travel card. It is one step in the booking, like checking the fare rules.
- Sign in to ShopBack US on the web or in the app.
- Open the booking site's page (Trip.com, Expedia or Priceline) and read which bookings qualify.
- Tap through and complete the booking, without detouring to coupon sites or other browser extensions.
Going through ShopBack gets you a cash rebate on the same order, at the same store. Cashback lowers what you actually pay for an order. It comes back as cash, so it works like a discount on the price, not like points or miles.
Rates change by booking site and campaign, so check the live rate on each site's ShopBack page before you book.
For how this works across flights, hotels and packages, see how to earn Cashback on travel bookings.
Paying with a travel card
You can usually pay with your normal travel credit card after going through ShopBack, but each part follows its own rules. Card points or miles depend on the card issuer's terms for travel purchases, and ShopBack's cash depends on the booking site's terms shown on its ShopBack page. Neither is guaranteed for every booking, and some fare types or payment methods can be excluded. Check both sets of terms before you pay, and see our guide on using ShopBack with credit cards for more.
Frequently asked questions
How do I find cheap flights to Chicago?
Search both Chicago airports, O'Hare (ORD) and Midway (MDW), with flexible dates, compare the identical flights and bags on two or three booking sites such as Expedia, Priceline and Trip.com, then check the airline's own site. Lock a good fare with the 24-hour hold or cancel rule, count the cost of getting downtown, and go through ShopBack US before you book so cash comes back on the same booking.
Is it cheaper to fly into O'Hare or Midway?
Neither is cheaper every time, so price both for your dates. According to Choose Chicago, O'Hare is about 17 miles from downtown with more than 1,000 direct daily flights, and Midway is about 10 miles from downtown. Both have a CTA train to the Loop: the Blue Line from O'Hare takes about 40 to 45 minutes and the Orange Line from Midway about 20 to 25 minutes, according to the CTA.
How do I find cheap flights to Denver?
Use the same method: flexible dates, the same flights compared on two or three booking sites, and the 24-hour rule to hold a fare. Denver International Airport (DEN) is the main airport, so the saving comes from timing and comparison rather than switching airports. According to Denver Union Station, the RTD A Line runs from downtown to DEN in about 37 minutes, which helps keep the whole trip cheap.
How do I find cheap flights to San Diego?
Compare the same flights into San Diego International Airport (SAN) across booking sites with flexible dates, and include Southwest in your search, since SAN says Southwest is its largest carrier and Priceline now sells Southwest fares. SAN sits about 3 miles northwest of downtown, according to the airport, so the ride into town is short.
How do I find cheap flights to New Orleans?
Avoid festival weekends if your dates are flexible, compare the same flights into Louis Armstrong New Orleans International Airport (MSY) on two or three booking sites, and check nonstop options from your city. According to New Orleans and Company, 15 airlines fly nonstop to New Orleans from about 50 destinations, and the RTA 202 Airport Express bus runs to downtown.
How do I find cheap flights to Nashville?
Search Nashville International Airport (BNA) with flexible dates, compare the same flights and bag allowance on two or three booking sites, and hold a fare with the 24-hour rule while you keep looking. According to WeGo Public Transit, the Route 18 bus links BNA with downtown Nashville for $2 each way at the time of writing, with express trips taking about 20 minutes.
What is the cheapest month to fly to Chicago?
There is no single cheapest month that holds every year, because fares move with demand, events and airline schedules. The reliable way to find it for your route is the month or calendar view on a booking site, which shows the lowest fare by day. Fares to Chicago are usually higher around holidays and big summer weekends, so midweek dates outside those periods tend to price lower.
Is Expedia or Priceline cheaper for flights to Chicago?
Neither is cheaper every time. Both search many airlines, so fares on the same flight are often close. Compare the exact same flight, time and bags on both on the same day. Priceline also sells Southwest fares, according to Priceline, which matters for Midway, Denver, San Diego, New Orleans and Nashville searches.
Can I use a Trip.com promo code and still get Cashback through ShopBack?
No. Go through ShopBack US to Trip.com and book without a code.
How does ShopBack lower what I pay for a flight?
Going through ShopBack gets you a cash rebate on the same order, at the same store. Cashback lowers what you actually pay for an order. It comes back as cash, so it works like a discount on the price, not like points or miles. The live rate for each booking site is shown on its ShopBack page.
Key takeaways
- Price O'Hare and Midway together for Chicago, with flexible dates.
- Compare the identical flights and bags on two or three booking sites, then hold a fare with the 24-hour rule.
- Before you book, go through ShopBack US: open Trip.com, Expedia or Priceline on ShopBack, tap through, then book.
Related reads
- How Do I Find Cheap Flights in 2026?
- How to Earn Cashback on Travel Bookings
- How to Save on Expedia
- Trip.com Discounts in the US
Book through ShopBack US: Trip.com · Expedia · Priceline · CheapOair · Booking.com · Hotels.com
Disclaimer
The views in this article are those of the author and are for general information only. Fares, schedules, transit fares and booking-site terms can change at any time; facts above are from the official sources named in each section at the time of writing. The current Cashback is shown on each booking site's ShopBack page before you book.
Related guides
How Do I Find Cheap Flights in 2026?
To find cheap flights in the US in 2026, search flexible dates and nearby airports, compare the same itinerary on Expedia, Priceline, CheapOair and Trip.com, use the airline's 24-hour hold or cancel rule to lock a fare, and go through ShopBack US before you book so part of the fare comes back as cash.
Earn Cashback on Hotels & Flights
Click through ShopBack before you book a flight, hotel, or activity. Cashback pays after the trip completes and the cancellation window closes.
Save on Expedia
Where the real Expedia US savings come from: One Key member pricing and OneKeyCash, Bundle deals, Member Only Deals, and why to go through ShopBack before you pay so part of the cost comes back when booking flights, hotels, cars, and packages.
Trip.com Discounts and Deals
Where the real Trip.com US savings live: Super Sale, Trip Coins, Trip.com Rewards member pricing, Black Friday and Travel Tuesday windows, and how to go through ShopBack before you book, with any Trip Coins redemption or member discount applied, so part of the cost comes back.
