Chicago from Cleveland, Oct 23–25: $1,408 for two, all in
The verdict
Our verdict
Worth it, if
- Fare is $358 per person, $109 below the typical fare
- Highs 68–72°F with a 5% to 12% rain chance
- Aloft by Marriott Chicago Mag Mile scores 8.1 from 2,536 reviews
The catch: The Frontier fare has 1 stop and takes 10h 52m overnight, and a checked bag is about $240 for two, not in the total.
Worth it if you can sleep through a long overnight connection for the lower fare; skip it if you'd rather pay $529 per person for the 1h 37m American nonstop.
Worth it if you can handle an overnight connection: $1,408 for two for Oct 23–25, 2026 (2 nights), which covers Frontier flights at $716 plus Aloft by Marriott Chicago Mag Mile at $597 and its $95 property fee, taxes and fees included. The Frontier fare isn't nonstop. It has 1 stop and takes 10h 52m, leaving Cleveland at 9:59 PM Friday and landing at O'Hare at 7:51 AM Saturday, and checked bags and spending money aren't in the total.
The total, before you go
$1,408 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
| For two | |
|---|---|
| Flights for two, round trip | $716 |
| Aloft by Marriott Chicago Mag Mile, 2 nights, two guests, taxes in | $597 |
| Resort fee, collected at the desk | $95 |
| The total, before you go | $1,408 |
| A checked bag each, round trip (not in the total) | about $240 |
$109 per person below the typical fare on this route.
Not in it: seat picks on basic fares and a checked bag (about $60 each way per bag on Frontier, $240 for two round trip); the resort fee is counted above. Prices are what we found at the time shown; the booking site’s checkout is the binding one.
The flight
$358 per person, round trip
$716 for two, taxes and fees included · Frontier · 1 stop · 10h 52m
Out Fri, Oct 23, 9:59 PM – Sat, Oct 24, 7:51 AM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | $358 | 1 stop | 10h 52m |
| American. Operated by Republic Airways as American Eagle | $529 | nonstop | 1h 37m |
| Frontier | $461 | 1 stop | 19h 34m |
Prices checked Oct 16, 2026, 12:31 AM EDT. 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
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Why now
At $358 per person, the Frontier fare is $109 below the typical fare on this route. That's 23% under it, and it sits at the bottom of the 12 offers we saw, which ran from $358 to $593. The whole trip comes to $1,408 for two with the Aloft's $95 property fee counted. A checked bag, about $240 for two, and spending money are extra. The forecast for Oct 23–25 is overcast, with highs of 68–72°F, lows of 58–59°F and rain chances of 5% to 12%, which is good weather for walking Millennium Park and taking a boat on the river. It's next weekend, so this is a short city getaway built around architecture, museums, deep-dish and blues at night. Prices were all-in when we found them and can change before you book.
The kind of trip this is
A fast city weekend for two: skyscraper architecture seen from the river, the Art Institute, deep-dish pizza and live blues after dark. It suits couples or friends who like to walk a lot and fill a Saturday, and who don't mind getting in on an overnight flight. The lakefront parks give you a break between museums and meals.
Weather in Chicago, Oct 23–25
Highs 68–72°F, little rain expected
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 23 | 72 °F | 59 °F | 5% |
| Sat, Oct 24 | 69 °F | 58 °F | 5% |
| Sun, Oct 25 | 68 °F | 58 °F | 12% |
Where to stay in Chicago
Aloft by Marriott Chicago Mag Mile is the best-value pick and the one in the total: $597 for the 2 nights ($299 a night) plus a $95 property fee, rated 8.1 from 2,536 reviews. It's in Magnificent Mile / Streeterville, which is good for shopping on Michigan Avenue and for the lakefront. Hampton Inn Chicago West Loop Fulton Market Area is the top rated at 8.8 from 776 reviews: $630 for the stay with breakfast, plus $100 paid at the property, and the West Loop puts you near the Randolph Street restaurant row. Congress Plaza Hotel Chicago is the budget option at $563 ($282 a night) plus $89 at the property, rated 7.1 from 4,525 reviews. It's the only one of the three with free cancellation, and it's in The Loop, close to Millennium Park and the theaters.
Aloft by Marriott Chicago Mag Mile
$597 for 2 nights, two guests · $299 a night
See roomsHampton Inn Chicago West Loop Fulton Market Area
$630 for 2 nights, two guests · $315 a night
See roomsCongress Plaza Hotel Chicago
$563 for 2 nights, two guests · $282 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 to see the skyline from the water
- See the Bean and the fountains in Millennium Park
- Eat deep-dish at Lou Malnati's or Pequod's
- Spend Saturday 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 Cleveland | Cleveland Hopkins International (CLE) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 10h 52m (1 stop) |
| Distance | 307 miles each way |
| Time difference | -1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | $716 |
| Hotel, 2 nights (Aloft by Marriott Chicago Mag Mile) | $597 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $1,833 |
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: Cleveland to Chicago
| Per person | |
|---|---|
| This trip | $358 per person |
| Lowest in the last 30 days | $345 (Oct 16, 2026) |
| Typical price, last 60 days | $467 |
| Price checks | 18 |
Good to know
- Passport: no passport needed for travelers from the United States: a government photo ID is enough for Chicago.
- Currency: US dollar (USD).
- No passport needed, you pay in US dollars, and Chicago is 1 hour behind Cleveland.
- The Frontier fare flies Cleveland Hopkins (CLE) to Chicago O'Hare (ORD) with 1 stop; return times weren't listed.
- An American Eagle nonstop was $529 per person, 1h 37m, leaving at 5:12 AM.
- Aloft and Hampton Inn don't offer free cancellation; Congress Plaza Hotel Chicago does.
- Checked bags run about $240 for two and aren't part of the $1,408.
Questions readers ask
Is it worth it?
Worth it if you can live with the overnight connection. The fare is $109 per person below the typical fare on this route, the forecast is mild and mostly dry, and the whole trip is $1,408 for two. The tradeoff is 10h 52m with 1 stop for a 307-mile trip.
How much is the whole trip for two?
$1,408 for two, all in: $716 for the Frontier flights, plus $597 for 2 nights at Aloft by Marriott Chicago Mag Mile and its $95 property fee, taxes and fees included. Checked bags (about $240 for two) and spending money are extra; our budget sets aside $520 for spending over the 2 days.
Do I need a passport?
No. It's a domestic trip, so your driver's license-style ID routine applies, and you'll set your watch back 1 hour when you land.
What is the weather like?
Overcast all three days. Highs are 72°F Friday, 69°F Saturday and 68°F Sunday, with lows of 58–59°F and rain chances of 5%, 5% and 12%. A light jacket covers the evenings.
Is 2 nights enough?
It's tight. You land at 7:51 AM Saturday, so you spend Friday night traveling and really get Saturday plus some of Sunday. That's enough for the river cruise, Millennium Park, the Art Institute, deep-dish and a blues set.
Is there a faster flight?
Yes. We saw an American Eagle nonstop at $529 per person that takes 1h 37m and leaves at 5:12 AM Friday. It isn't in the $1,408 total.
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Worth it if one evening on the Gulf is all you're after; skip it if you want a real weekend on the beach.
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