Chicago from Baltimore, Oct 16–18: round trip from $340
A round trip from Baltimore to Chicago costs $340 per person ($679 for two) for Oct 16–18, 2026, which is 2 nights, nonstop on F9. After an overcast Friday, the forecast shows highs of 52–62°F and little rain. The best-value hotel, Cambria Hotel Chicago Loop - Theatre District, is $882 for the stay.
The flight
$340 per person, round trip
$679 for two, taxes and fees included · Frontier · nonstop · 4h 26m
Out Fri, Oct 16, 9:58 AM – Fri, Oct 16, 11:21 AM · back Sun, Oct 18, 6:00 AM – Sun, Oct 18, 9:03 AM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | $340 | nonstop | 4h 26m |
| Frontier | $361 | 1 stop | 13h 2m |
| Frontier | $361 | 1 stop | 13h 18m |
Prices checked Oct 12, 2026, 11:15 PM 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 | $679 |
| Cambria Hotel Chicago Loop - Theatre District, 2 nights | $882 |
| Trip total for two | $1,561 |
Tweak this trip
Why go now
At $340 per person round trip and nonstop, this fare matches the median of the 9 earlier checks we ran on this route. That makes it a fair price, not a markdown. The lowest we saw was $321 on Oct 13. The real draw is how the weekend is laid out. A 9:58 AM Friday departure lands at O'Hare at 11:21 AM local time, so you're there in time for lunch in The Loop. Friday looks overcast at 56°F with a 56% chance of rain. Saturday turns mostly clear at 52°F, and Sunday is clear at 62°F. That's jacket weather, good for a river cruise, museums and deep-dish. Our rough budget for two comes to $2,082. That covers flights, the best-value hotel and $130 a day each for spending.
The kind of trip this is
This is a compact city weekend built around architecture, museums, food and live music. It suits a couple or two friends who like to walk a lot and eat well, with one full day in the middle. The pace is brisk. Friday afternoon and Saturday do most of the work, and the 6:00 AM Sunday flight means calling it an early night on Saturday.
Weather in Chicago, Oct 16–18
Highs 52–62°F, little rain expected
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 16 | 56 °F | 46 °F | 56% |
| Sat, Oct 17 | 52 °F | 44 °F | 1% |
| Sun, Oct 18 | 62 °F | 45 °F | 1% |
Where to stay in Chicago
All three picks are in The Loop, which puts architecture, theatres and Millennium Park at your doorstep. Cambria Hotel Chicago Loop - Theatre District is the best value: $882 for the 2 nights ($441 a night), an 8.1 review score from 1,256 reviews, and free cancellation. Canopy By Hilton Chicago Central Loop is the top rated at 8.9 from 308 reviews. It's $962 for the stay ($481 a night), but it isn't free to cancel. Congress Plaza Hotel Chicago is the budget pick at $778 ($389 a night) and scores 7.1 from 4,548 reviews. That price gets a king room with a lake view, plus free cancellation. All three are room only. If dinner matters most, West Loop has the restaurant row on Randolph Street.
Cambria Hotel Chicago Loop - Theatre District
$882 for 2 nights, two guests · $441 a night
See roomsCanopy By Hilton Chicago Central Loop
$962 for 2 nights, two guests · $481 a night
See roomsCongress Plaza Hotel Chicago
$778 for 2 nights, two guests · $389 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 on Saturday, the mostly clear day.
- See the Bean and the fountains in Millennium Park, right in The Loop.
- Eat deep-dish at Lou Malnati's or Pequod's.
- Spend the overcast Friday afternoon at the Art Institute of Chicago.
- Hear live blues at Kingston Mines on Saturday night.
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 Baltimore | Baltimore/Washington International Thurgood Marshall (BWI) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 4h 26m nonstop |
| Distance | 604 miles each way |
| Time difference | -1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | $680 |
| Hotel, 2 nights (Cambria Hotel Chicago Loop - Theatre District) | $882 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $2,082 |
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: Baltimore to Chicago
| Per person | |
|---|---|
| This trip | $340 per person |
| Lowest in the last 30 days | $321 (Oct 13, 2026) |
| Typical price, last 60 days | $340 |
| Price checks | 9 |
Good to know
- Passport: not needed for US citizens; a government ID is enough.
- Currency: US dollar (USD).
- No passport needed, the currency is the US dollar, and Chicago is 1 hour behind Baltimore.
- The outbound leaves BWI at 9:58 AM on Friday, Oct 16 and lands at ORD at 11:21 AM local time.
- The return leaves at 6:00 AM on Sunday, Oct 18 and lands at 9:03 AM, so plan an early start.
- All hotels are room only. Cambria and Congress Plaza offer free cancellation; Canopy doesn't.
- Prices are all-in, with taxes and fees, as found when we checked. They can change before you book.
Questions readers ask
How much is the flight?
It's $340 per person, or $679 for two, round trip and nonstop on F9. That's all-in with taxes and fees as of when we checked. The next option we found was $361 per person with one stop.
Is $340 a good price for this route?
It's a fair price. It matches the median of the 9 earlier checks we ran on this route, so it isn't a discount. The low was $321 on Oct 13. Prices move, so check the live fare before you book.
Do I need a passport?
No. It's a domestic trip, you'll pay in US dollars, and Chicago is just 1 hour behind Baltimore.
What is the weather like?
Friday looks overcast with a high of 56°F and a 56% chance of rain. Saturday is mostly clear at 52°F, and Sunday is clear at 62°F. Lows run from 44°F to 46°F, so pack a warm layer.
Is 2 nights enough?
For a quick city break, yes. You land at 11:21 AM Friday and get a full Saturday. The return leaves at 6:00 AM Sunday, so Sunday is just the trip home.
What does the whole weekend cost for two?
Our rough budget is $2,082 for two. That's $680 for flights, $882 for the best-value hotel and $520 for spending, which works out to $130 a day per person.
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Chicago in pictures
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Image credits
- Photo: Joshua Santos / Pexels, Pexels License
- Photo: K / Pexels, Pexels License
- Photo: Mik Dominguez / Pexels, Pexels License