Chicago from Washington, DC, Oct 16–18: round trip from $354
Round trip from Washington, DC to Chicago is $354 per person ($708 for two), all-in, for Oct 16–18, 2026, 2 nights, on Frontier with 1 stop. After a drizzly Friday, expect highs of 52–61°F with little rain. Holiday Inn Chicago Midway Airport S by IHG is the best-value stay at $485 for both nights.
The flight
$354 per person, round trip
$708 for two, taxes and fees included · Frontier · 1 stop · 7h 24m
Out Fri, Oct 16, 6:00 PM – Sat, Oct 17, 12:24 AM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | $354 | 1 stop | 7h 24m |
| United | $493 | nonstop | 2h 15m |
| American | $493 | nonstop | 2h 26m |
Prices checked Oct 12, 2026, 4:01 AM EDT. Prices change; the binding price is the one on the booking site.
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Your trip for two
| For two | |
|---|---|
| Flights for two | $708 |
| Holiday Inn Chicago Midway Airport S by IHG, 2 nights | $485 |
| Trip total for two | $1,193 |
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Why go now
$354 per person is $12 under the $366 median of our earlier checks on this route, about 3% less, and it's the lowest fare we've seen in 30 days. That's $708 for two, all-in, as of when we checked. Fares move, so treat it as a snapshot. Our budget comes to $1,713 for two: $708 for flights, $485 for the best-value hotel and $520 for spending. Mid-October makes for a cool-weather city weekend. Friday shows 60°F with a 33% chance of drizzle, Saturday 52°F and mostly clear, and Sunday 61°F and clear. Pack a sweater for walking the lakefront, a river cruise past the skyscrapers and long dinners indoors. If you'd rather land Friday morning, the nonstops on United and American run $493 per person.
The kind of trip this is
This is a city weekend built around food, architecture and live music. It suits a couple or two friends who like to walk a lot and eat well, with a museum morning and a blues club night mixed in. The pace is quick. The Frontier fare lands after midnight, so you really get one full day plus Sunday, and it pays to plan a packed first morning.
Weather in Chicago, Oct 16–18
Highs 52–61°F, little rain expected
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 16 | 60 °F | 45 °F | 33% |
| Sat, Oct 17 | 52 °F | 44 °F | 4% |
| Sun, Oct 18 | 61 °F | 45 °F | 6% |
Where to stay in Chicago
Holiday Inn Chicago Midway Airport S by IHG is the best-value pick: $485 for both nights ($243 a night) in a Standard King Room. It has a review score of 7.5 from 226 reviews, it's room only and there's no free cancellation. Sleep Inn Midway Airport is the budget pick at $369 ($185 a night), with a score of 7.3 from 726 reviews, breakfast included and free cancellation. Hyatt Regency McCormick Place Chicago in the South Loop is the top-rated pick at $1,020 ($510 a night), with a score of 8.5 from 998 reviews and free cancellation. Heads-up: two of these hotels carry Midway in their names, but the Frontier flight lands at O'Hare. To sleep central, look in The Loop for architecture, theatres and Millennium Park, or River North for galleries, steakhouses and nightlife.
Holiday Inn Chicago Midway Airport S by IHG
$485 for 2 nights, two guests · $243 a night
See roomsHyatt Regency McCormick Place Chicago
$1,020 for 2 nights, two guests · $510 a night
See roomsSleep Inn Midway Airport
$369 for 2 nights, two guests · $185 a night
See roomsAll hotels in Chicago for these dates
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Where in Chicago
- The Loop: Architecture, theatres and Millennium Park at your doorstep.
- Magnificent Mile / Streeterville: Shopping on Michigan Avenue and lakefront hotels.
- River North: Galleries, steakhouses and the city's nightlife core.
- West Loop: Converted warehouses with the top restaurant row on Randolph Street.
- Lincoln Park: Leafy neighbourhood with a free zoo and lakefront beaches.
What to do in Chicago
- Take the Chicago Architecture Foundation river cruise for the skyline from the water.
- See the Bean and the fountains in Millennium Park, an easy walk from The Loop.
- Eat deep-dish at Lou Malnati's or Pequod's, or try both and pick a side.
- Spend a morning at the Art Institute of Chicago.
- Hear live blues at Kingston Mines on Saturday night.
- Walk Randolph Street in the West Loop for its restaurant row.
Also worth it
- Visit the Art Institute of Chicago
- Catch a Cubs game at Wrigley Field
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Getting there and around
| Airports in Washington, DC | Ronald Reagan Washington National (DCA), Washington Dulles International (IAD), Baltimore/Washington International Thurgood Marshall (BWI) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 7h 24m (1 stop) |
| Distance | 593 miles each way |
| Time difference | -1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | $708 |
| Hotel, 2 nights (Holiday Inn Chicago Midway Airport S by IHG) | $485 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $1,713 |
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: Washington, DC to Chicago
| Per person | |
|---|---|
| This trip | $354 per person |
| Lowest in the last 30 days | $354 (Oct 12, 2026) |
| Typical price, last 60 days | $366 |
| Price checks | 8 |
Good to know
- Passport: not needed for US citizens; a government ID is enough.
- Currency: US dollar (USD).
- No passport needed. It's a domestic trip, and you'll pay in US dollars.
- Chicago is 1 hour behind Washington, DC.
- The $354 Frontier fare has 1 stop and takes 7h 24m, leaving DCA at 6:00 PM Friday and landing at ORD at 12:24 AM Saturday.
- Free cancellation comes with the Hyatt Regency McCormick Place Chicago and Sleep Inn Midway Airport, but not with the Holiday Inn.
- Of the three hotels, only Sleep Inn Midway Airport includes breakfast.
Questions readers ask
How much is the flight?
We found $354 per person round trip on Frontier, or $708 for two, all-in with taxes and fees. That's 3% under the $366 median of our earlier checks and the lowest in 30 days. Prices can change after we check.
Is there a nonstop option?
Yes. United leaves at 8:30 AM and American at 8:41 AM on Friday, Oct 16, both nonstop and both $493 per person. That's $139 per person more than Frontier, but you land in the morning instead of after midnight.
Do I need a passport?
No. Chicago is a domestic trip from Washington, DC, and the currency is the US dollar. The only adjustment is the clock: Chicago is 1 hour behind.
What is the weather like?
Friday shows 60°F with a 33% chance of drizzle. Saturday looks mostly clear at 52°F, and Sunday is clear at 61°F. Lows sit at 44–45°F, so bring a warm layer for evenings.
Is 2 nights enough?
For a fast city weekend, yes, if you plan ahead. On the Frontier fare you land at 12:24 AM Saturday, so you get one full day plus Sunday. That's room for a river cruise, the Art Institute, deep-dish and one blues night.
What does the whole weekend cost?
Our budget comes to $1,713 for two: $708 for flights, $485 for two nights at Holiday Inn Chicago Midway Airport S by IHG, and $520 for spending, which works out to $130 a day per person.
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Image credits
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