Chicago from Minneapolis, Oct 16–18: $1,603 for two, all in
The verdict
Our verdict
Worth it, if
- $378 per person, $19 below the typical fare on this route
- Hyatt Centric in The Loop: 8.5 from 1,003 reviews, free cancellation
- Sunday is clear and 65°F with a 0% chance of rain
The catch: The Frontier fare has one stop and takes 8h 58m for 355 miles, landing at 6:31 PM Friday, a day with an 82% chance of drizzle.
Worth it if you'd trade Friday's travel time for the lower fare; skip it if you'd pay $557 per person for American's 1h 44m nonstop.
Worth it if you can give up Friday to travel: $1,603 for two is the Frontier round trip at $756 plus 2 nights at Hyatt Centric The Loop Chicago at $847, taxes and fees included. The trip runs Oct 16–18, 2026, 2 nights, and the Frontier flight isn't nonstop: one stop, 8h 58m on the way out. Resort fees, a checked bag and spending money aren't in that total.
The total, before you go
$1,603 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, round trip | $756 |
| Hyatt Centric The Loop Chicago, 2 nights, two guests, taxes in | $847 |
| The total, before you go | $1,603 |
| A checked bag each, round trip (not in the total) | about $240 |
$19 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); 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
$378 per person, round trip
$756 for two, taxes and fees included · Frontier · 1 stop · 8h 58m
Out Fri, Oct 16, 9:33 AM – Fri, Oct 16, 6:31 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | $378 | 1 stop | 8h 58m |
| American | $557 | nonstop | 1h 44m |
| Sun Country | $443 | 1 stop | 14h 42m |
Prices checked Oct 14, 2026, 5:17 AM CDT. Prices change; the binding price is the one on the booking site.
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Why now
At $378 per person, the Frontier fare is $19 below the typical fare on this route, about 5% under, and it's the lowest of the 12 offers we checked, which went as high as $557. Our 9 earlier checks put the median at $397 and the low at $364, so it's a fair price, not a record. The forecast suits a city weekend once you're there. Friday has an 82% chance of drizzle and a high of 58°F. Saturday is overcast at 58°F with a 12% chance of rain, and Sunday clears to 65°F. That's jacket weather for the river cruise and an indoor afternoon at the Art Institute. Mid-October falls between summer's lakefront season and the holiday markets, so this weekend is about museums, food and blues, not festivals.
The kind of trip this is
A city weekend for two: architecture, museums, deep-dish and live blues, at an easy walking pace from a base in The Loop. It suits a couple or two friends who like to wander, eat well and stay out for music on Saturday night. Since Friday mostly goes to getting there, plan the trip around two full days on Saturday and Sunday.
Weather in Chicago, Oct 16–18
Highs 58–65°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 16 | 58 °F | 48 °F | 82% |
| Sat, Oct 17 | 58 °F | 45 °F | 12% |
| Sun, Oct 18 | 65 °F | 49 °F | 0% |
Where to stay in Chicago
Our pick is Hyatt Centric The Loop Chicago: $847 for both nights ($424 a night) in a King Room, rated 8.5 from 1,003 reviews, room only, with free cancellation. It's the best value and the hotel in the $1,603 total. The top rated is Riu Plaza Chicago in Streeterville, 9.1 from 8,463 reviews, with breakfast included, at $1,368 for the stay ($684 a night) and no free cancellation. Club Quarters Hotel Central Loop, Chicago has 8.2 from 5,339 reviews at $893 ($447 a night), room only, with no free cancellation. It costs more than the Hyatt this weekend. The Loop puts architecture, theaters and Millennium Park at your doorstep, and Magnificent Mile / Streeterville is the area for Michigan Avenue shopping and lakefront hotels.
Hyatt Centric The Loop Chicago
$847 for 2 nights, two guests · $424 a night
See roomsRiu Plaza Chicago
$1,368 for 2 nights, two guests · $684 a night
See roomsClub Quarters Hotel Central Loop, Chicago
$893 for 2 nights, two guests · $447 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 dry, overcast Saturday
- See the Bean and the fountains in Millennium Park, steps from The Loop hotels
- Eat deep-dish at Lou Malnati's or Pequod's
- Spend the drizzly hours inside the Art Institute of Chicago
- Hear live blues at Kingston Mines on Saturday night
- Catch a Cubs game at Wrigley Field if one is on
Also worth it
- Visit the Art Institute of Chicago
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Getting there and around
| Airports in Minneapolis | Minneapolis-Saint Paul International (MSP) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 8h 58m (1 stop) |
| Distance | 355 miles each way |
| Time difference | same time zone |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | $756 |
| Hotel, 2 nights (Hyatt Centric The Loop Chicago) | $847 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $2,123 |
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: Minneapolis to Chicago
| Per person | |
|---|---|
| This trip | $378 per person |
| Lowest in the last 30 days | $364 (Oct 13, 2026) |
| Typical price, last 60 days | $397 |
| Price checks | 9 |
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, the currency is the US dollar, and Chicago is on the same time as Minneapolis.
- The Frontier flight leaves MSP at 9:33 AM Friday and lands at O'Hare (ORD) at 6:31 PM after one stop.
- Chicago also has Midway (MDW), but this fare flies into O'Hare.
- Only Hyatt Centric The Loop Chicago has free cancellation. Riu Plaza Chicago and Club Quarters don't.
- Prices are all in as we found them and can change. Resort fees and a checked bag aren't included.
Questions readers ask
Is it worth it?
Yes, if you don't mind a long Friday. The fare is $19 per person below the typical fare on this route and the hotel is rated 8.5 with free cancellation, but the flight has one stop and takes 8h 58m to cover 355 miles.
How much is the whole trip for two?
It's $1,603 all in: $756 for two Frontier round trips plus $847 for 2 nights at Hyatt Centric The Loop Chicago. Resort fees and a checked bag aren't included. With our $520 estimate for spending money, the budget comes to $2,123.
Is there a nonstop?
Yes. American flies nonstop at 5:25 AM and lands at 7:09 AM, 1h 44m, for $557 per person, or $1,114 for two. It costs more, but it gives you all of Friday in the city.
What is the weather like?
Friday has a high of 58°F and an 82% chance of drizzle. Saturday is overcast at 58°F with a 12% chance of rain. Sunday is clear at 65°F with a 0% chance. Bring a jacket.
Do I need a passport?
No. It's a domestic trip, the currency is the US dollar, and Chicago is on the same time as Minneapolis.
Is 2 nights enough?
For a city weekend, yes, if you plan around Saturday and Sunday. You land at 6:31 PM Friday, so treat that night as dinner and an early start.
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All trips from Minneapolis · Chicago from every city · Prices on this route · Trips in October 2026 · Home
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