Washington, D.C. from Chicago, Oct 23–25: $1,565 for two, all in
The verdict
Our verdict
Worth it, because
- United nonstop from O'Hare, 2h 8m, landing 1:08 PM Friday
- Fare $478 per person, $50 below the typical fare on this route
- citizenM Georgetown scores 9 from 275 reviews, with free cancellation
The catch: Resort fees, a checked bag and spending money aren't in the $1,565, and nights drop to 40°F, so pack a warm layer.
Worth it if you want museums, monuments and long walks in cool fall air; skip it if you're after beach weather.
Worth it for the two of you: $1,565 for two, all in, which is the flights at $956 plus citizenM Washington DC Georgetown at $609, taxes and fees included. That covers Oct 23–25, 2026, 2 nights, on a United nonstop from O'Hare to Reagan National. Resort fees, a checked bag and spending money are not in the total.
The total, before you go
$1,565 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, round trip | $956 |
| citizenM Washington DC Georgetown, 2 nights, two guests, taxes in | $609 |
| The total, before you go | $1,565 |
| A checked bag each, round trip (not in the total) | about $160 |
$50 per person below the typical fare on this route.
Not in it: seat picks on basic fares and a checked bag (about $40 each way per bag on United, $160 for two round trip); a resort fee, if the hotel has one, is collected at the desk. Prices are what we found at the time shown; the booking site’s checkout is the binding one.
The flight
$478 per person, round trip
$956 for two, taxes and fees included · United · nonstop · 2h 8m
Out Fri, Oct 23, 10:00 AM – Fri, Oct 23, 1:08 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| United | $478 | nonstop | 2h 8m |
| American | $478 | nonstop | 2h 6m |
| United | $478 | nonstop | 2h 8m |
Prices checked Oct 14, 2026, 12:59 AM CDT. Prices change; the binding price is the one on the booking site.
Paid links: when you book through a link on this page, the booking site pays us a referral fee. Your price does not change. How we earn
Tweak this trip
Why now
At $478 per person, the fare is $50 below the typical fare on this route, which is $528, so you're paying 9% less. We saw 12 offers and all came in at $478 per person, with nonstops on United and American. Add citizenM Washington DC Georgetown at $609 for 2 nights and the trip comes to $1,565 for two, taxes and fees included. The forecast works well for walking: highs of 54°F Friday, 58°F Saturday and 62°F Sunday, with rain chances between 5% and 19%. Cherry blossom season is in the spring, so this one's a museums-and-monuments weekend. The 10:00 AM departure lands at 1:08 PM, which leaves Friday afternoon for a first museum. Washington is 1 hour ahead of Chicago, so set your watch when you land.
The kind of trip this is
A city and history weekend at an easy pace: free Smithsonian museums, the monuments of the National Mall and dinners at the Wharf, all linked by the Metro. It suits a couple or two friends who like to walk, read every plaque and end the day at a good table. Two nights gives you a good taste of the city without rushing.
Weather in Washington, D.C., Oct 23–25
Highs 54–62°F, little rain expected
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 23 | 54 °F | 44 °F | 5% |
| Sat, Oct 24 | 58 °F | 40 °F | 19% |
| Sun, Oct 25 | 62 °F | 45 °F | 16% |
Where to stay in Washington, D.C.
Our pick is citizenM Washington DC Georgetown: $609 for the stay ($305 a night), rated 9 from 275 reviews, a King Room with North View and free cancellation. It's the best value. Georgetown gives you cobbled streets, canal walks and shopping. Mint House Washington Dc Downtown By Kasa is the top rated at 9.1 from 1,113 reviews, $612 for the stay ($306 a night); heads-up, it has no free cancellation. Wyndham Garden Washington DC North is the budget choice at $373 for the stay ($187 a night), 3 stars, 7.4 from 3,393 reviews, with breakfast and free cancellation. If you'd rather walk to the museums and the White House, Downtown / Penn Quarter is the area for that.
citizenM Washington DC Georgetown
$609 for 2 nights, two guests · $305 a night
See roomsMint House Washington Dc Downtown By Kasa
$612 for 2 nights, two guests · $306 a night
See roomsWyndham Garden Washington DC North
$373 for 2 nights, two guests · $187 a night
See roomsAll hotels in Washington, D.C. for these dates
Paid links: when you book through a link on this page, the booking site pays us a referral fee. Your price does not change. How we earn
Where in Washington, D.C.
- Downtown / Penn Quarter: Walk to the National Mall, museums and the White House.
- Dupont Circle: Embassy-row townhouses, cafes and quick Metro links.
- Georgetown: Cobbled streets, canal walks and upscale shopping.
- Capitol Hill / Navy Yard: Near the Capitol, Eastern Market and the ballpark.
- Arlington, VA: Lower rates one Metro stop from the monuments.
What to do in Washington, D.C.
- Walk the National Mall from the Capitol to the Lincoln Memorial on clear Saturday
- Visit the National Air and Space Museum and the Natural History Museum, both free Smithsonian museums
- Tour the Capitol and the Library of Congress
- Pay respects at Arlington National Cemetery, an easy Metro ride from the monuments
- Dine along the Wharf on the Southwest waterfront for your last night
Also worth it
- See the cherry blossoms around the Tidal Basin
Tours and tickets in Washington, D.C.
Paid links: when you book through a link on this page, the booking site pays us a referral fee. Your price does not change. How we earn
Getting there and around
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
|---|---|
| Airports in Washington, D.C. | Reagan Washington National (DCA), Washington Dulles International (IAD), Baltimore/Washington International (BWI) |
| Flight time | 2h 8m nonstop |
| Distance | 594 miles each way |
| Time difference | +1 hour |
What 2 nights in Washington, D.C. costs
| Estimate | |
|---|---|
| Flights for two | $956 |
| Hotel, 2 nights (citizenM Washington DC Georgetown) | $609 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $2,085 |
Flights and hotel are the prices we found; spending is a planning estimate for an upscale destination, per person per day times two.
Price history: Chicago to Washington, D.C.
| Per person | |
|---|---|
| This trip | $478 per person |
| Lowest in the last 30 days | $354 (Oct 12, 2026) |
| Typical price, last 60 days | $528 |
| Price checks | 16 |
Good to know
- Passport: no passport needed for travelers from the United States: a government photo ID is enough for Washington, D.C..
- Currency: US dollar (USD).
- No passport needed: it's a domestic trip and you pay in US dollars.
- Washington is 1 hour ahead of Chicago; the flight covers 594 miles in 2h 8m.
- Return flight times weren't in our check, so confirm them on the airline's site.
- Prices are all-in as found when we checked and can change; resort fees and a checked bag aren't included.
- For spending money our budget allows $130 per person a day, $520 for two, for $2,085 in all.
Questions readers ask
Is it worth it?
Yes, for a city weekend: a nonstop of 2h 8m, a fare $50 below the typical fare on this route, and a hotel rated 9 with free cancellation.
How much is the whole trip for two?
$1,565 all in: $956 for two round-trip fares at $478 per person plus $609 for 2 nights at citizenM Washington DC Georgetown. Resort fees, a checked bag and spending money aren't in it; with $520 for spending, our budget comes to $2,085.
What is the weather like?
The forecast shows highs of 54°F, 58°F and 62°F, lows down to 40°F, and rain chances of 5% to 19%. Mostly clear Friday, clear Saturday, overcast Sunday. Bring a jacket.
Is 2 nights enough?
Enough for the Mall, one or two Smithsonian museums and a dinner at the Wharf. Landing at 1:08 PM Friday gives you an afternoon on top of a full Saturday.
Do I need a passport?
No. It's a domestic flight from O'Hare to Reagan Washington National (DCA), and you pay in US dollars.
Which airports does this use?
The fare we found flies ORD to DCA. Washington also has Dulles (IAD) and Baltimore/Washington (BWI), and Chicago also has Midway (MDW).
Also found for you
The newest finds from Chicago.
Just found · from ChicagoNot worth it this week
Asheville
Oct 23–25, 2026 · 2 nights
- Clear skies Friday and Saturday, highs of 69°F and 71°F
- Comfort Suites Outlet Center: 8.2 from 556 reviews, breakfast included
- October is peak fall foliage on the Blue Ridge Parkway
$1,581 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights $1,053 + hotel $474 + resort fee $54, taxes in · a checked bag each adds about $240
F9 + G4 · with a stop · 39h 13m
The catch: The $527 fare has 2 stops and takes 39h 13m, landing Saturday at 6:00 PM, and a checked bag is about $240 for two.
Worth it if you switch to the $579 nonstop and want foliage and breweries; skip this 2-stop fare if you want a real weekend.
Tweak this trip
Just found · from ChicagoLowest in 30 daysWorth it, if
Nashville
Oct 23–25, 2026 · 2 nights
- $366 per person, $37 below the typical fare on this route
- Breakfast included at Sonesta Select, rated 8.7 from 2,186 reviews
- Highs of 71–85°F with rain chances of 20% or less
$1,192 for two · 2 nights · flights, hotel, taxes & fees
Flights $732 + hotel $460, taxes in · a checked bag each adds about $240
Frontier · with a stop · 12h 42m
The catch: The Frontier outbound has one stop and takes 12h 42m, leaving 8:11 PM Friday and landing 8:53 AM Saturday.
Worth it if you want a Saturday of honky-tonks and hot chicken for less; skip it if you need a full Friday night in town.
Tweak this trip
Just found · from ChicagoWorth it, if
Cancún
Nov 14–21, 2026 · 7 nights
- Nonstop from O'Hare: leave 6:10 AM, land in Cancún 11:08 AM
- Aloft by Marriott Cancun: 8.1 from 798 reviews, free cancellation
- $404 per person, right at the $404 median of 13 checks
$1,601 for two · 7 nights · flights, hotel, taxes & fees
Flights $807 + hotel $794, taxes in · a checked bag each adds about $240
Frontier · nonstop · 7h 59m
The catch: Weather normals for these dates show drizzle most days and rain on two, and a checked bag is about $240 for two, not in the total.
Worth it if you want a warm, easy beach week at a fair fare; skip it if gray, drizzly days would spoil the trip for you.
Tweak this trip
More trips
Next weekend · from ChicagoWorth it, if
Orlando
Oct 16–18, 2026 · 2 nights
- Nonstop on Frontier, ORD to MCO in 2h 57m
- $280 per person, $10 under the typical $290 on this route
- Breakfast included at a hotel rated 8 from 4,289 reviews
$817 for two · 2 nights · flights, hotel, taxes & fees
Flights $560 + hotel $257, taxes in · a checked bag each adds about $240
Frontier · nonstop · 2h 57m
The catch: You land just after midnight, so this is really a Saturday and Sunday, and a checked bag is about $240 for two, which isn't in the total.
Worth it if the two of you want one big park day on a short budget; skip it if you want a slow, unhurried vacation.
The weekend after · from Chicago21% below typicalWorth it, if
Great Smoky Mountains
Oct 23–25, 2026 · 2 nights
- $429 per person, $118 below the typical fare on this route
- Zoders Inn and Suites in Gatlinburg, 8.2 from 1,812 reviews
- Peak fall foliage, highs of 59–66°F, 10% rain Friday and Saturday
$1,142 for two · 2 nights · flights, hotel, taxes & fees
Flights $858 + hotel $284, taxes in · a checked bag each adds about $140
Delta · with a stop · 4h 27m
The catch: The $429 fare has one stop and leaves O'Hare at 5:27 AM, and late October brings the busiest weekends of the year.
Worth it if you want fall color and mountain trails for a weekend and don't mind crowds; skip it if you need a quiet park.
A week away · from ChicagoLowest in 30 daysWorth it, if
New York City
Nov 14–21, 2026 · 7 nights
- $244 per person, $104 below the typical fare on this route
- Pod 51 scores 8.2 from 9,513 reviews, with free cancellation
- Met or MoMA mornings, highs of 45–55°F for walking the High Line
$2,088 for two · 7 nights · flights, hotel, taxes & fees
Flights $488 + hotel $1,600, taxes in · a checked bag each adds about $240
Frontier · with a stop · 9h 30m
The catch: The Frontier fare has one stop and takes 9h 30m, and Pod 51's room is a bunk pod with a shared bathroom.
Worth it if a long travel day and a bunk pod are fine for a week in New York; skip it if you need a private bathroom.
Just found · from ChicagoNot worth it this week
Asheville
Oct 23–25, 2026 · 2 nights
- Clear skies Friday and Saturday, highs of 69°F and 71°F
- Comfort Suites Outlet Center: 8.2 from 556 reviews, breakfast included
- October is peak fall foliage on the Blue Ridge Parkway
$1,581 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights $1,053 + hotel $474 + resort fee $54, taxes in · a checked bag each adds about $240
F9 + G4 · with a stop · 39h 13m
The catch: The $527 fare has 2 stops and takes 39h 13m, landing Saturday at 6:00 PM, and a checked bag is about $240 for two.
Worth it if you switch to the $579 nonstop and want foliage and breweries; skip this 2-stop fare if you want a real weekend.
Just found · from ChicagoLowest in 30 daysWorth it, if
Nashville
Oct 23–25, 2026 · 2 nights
- $366 per person, $37 below the typical fare on this route
- Breakfast included at Sonesta Select, rated 8.7 from 2,186 reviews
- Highs of 71–85°F with rain chances of 20% or less
$1,192 for two · 2 nights · flights, hotel, taxes & fees
Flights $732 + hotel $460, taxes in · a checked bag each adds about $240
Frontier · with a stop · 12h 42m
The catch: The Frontier outbound has one stop and takes 12h 42m, leaving 8:11 PM Friday and landing 8:53 AM Saturday.
Worth it if you want a Saturday of honky-tonks and hot chicken for less; skip it if you need a full Friday night in town.
All trips from Chicago · Washington, D.C. from every city · Prices on this route · Trips in October 2026 · Home
Washington, D.C. in pictures
Paid links: when you book through a link on this page, the booking site pays us a referral fee. Your price does not change. We use AI tools to draft the text of each page from the data on it; code checks every number in the draft against that data and rejects what does not match, and the team reviews pages and fixes or removes what readers report. How we pick · Report a mistake.
Image credits
- Photo: Mike Gordon / Pexels, Pexels License
- Photo: Paula Nardini / Pexels, Pexels License
- Photo: Mike Gordon / Pexels, Pexels License