$65 Cheap flight deals from Brainerd (MSP) to Chicago (CHI)

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This Weekend's Flight Deals from Brainerd to Chicago

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, May 11 - Mon, May 12
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$192 Roundtrip, just found
$192
Roundtrip
just found
Select Sun Country Airlines flight, departing Sun, May 11 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Mon, May 12, priced at $192 just found
Sun, May 11 - Tue, May 13
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$387 Roundtrip, found 5 days ago
$387
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Sun, May 11 from Minneapolis - St. Paul Intl. to Midway Intl., returning Tue, May 13, priced at $387 found 5 days ago

Airfares from $65 One Way, $128 Round Trip from Brainerd to Chicago

Prices starting at $128 for return flights and $65 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Jun 6 - Sun, Jun 8
MSP
Minneapolis
ORD
Chicago
$128 Roundtrip, just found
$128
Roundtrip
just found
Select Sun Country Airlines flight, departing Fri, Jun 6 from Minneapolis to Chicago, returning Sun, Jun 8, priced at $128 just found
Thu, Nov 27 - Mon, Dec 1
MSP
Minneapolis
ORD
Chicago
$137 Roundtrip, found 6 hours ago
$137
Roundtrip
found 6 hours ago
Select Sun Country Airlines flight, departing Thu, Nov 27 from Minneapolis to Chicago, returning Mon, Dec 1, priced at $137 found 6 hours ago
Thu, May 29 - Mon, Jun 2
MSP
Minneapolis
ORD
Chicago
$139 Roundtrip, just found
$139
Roundtrip
just found
Select Sun Country Airlines flight, departing Thu, May 29 from Minneapolis to Chicago, returning Mon, Jun 2, priced at $139 just found
Fri, Aug 15 - Sun, Aug 17
MSP
Minneapolis
ORD
Chicago
$170 Roundtrip, found 1 hour ago
$170
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, Aug 15 from Minneapolis to Chicago, returning Sun, Aug 17, priced at $170 found 1 hour ago
Sat, May 31 - Tue, Jun 3
MSP
Minneapolis
MDW
Chicago
$173 Roundtrip, just found
$173
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, May 31 from Minneapolis to Chicago, returning Tue, Jun 3, priced at $173 just found

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (1,605 reviews)

Jun 12 - Jun 15

3 night stay

Minneapolis (MSP) to Chicago (ORD)

Sun Country Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Our second time. Here, highly recommended

Reviewed on Mar 3, 2025

Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

9/10 Wonderful! (295 reviews)

Jun 12 - Jun 15

3 night stay

Minneapolis (MSP) to Chicago (ORD)

Sun Country Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Front desk and maintenance staff was amazing super succeeded our expectations i will return gor future dates

Reviewed on Feb 16, 2024

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More About Flying To Chicago from Brainerd

Route Information for Flights from Brainerd to Chicago

Origin Airport IATA Code
MSP
Destination Airport IATA Code
CHI
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Brainerd to Chicago

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Frequently asked questions

Are there non-stop flights from Brainerd to Chicago?
Nonstop flights are offered by no less than 4 airlines from Minneapolis, MN (MSP-Minneapolis - St. Paul Intl.) to O’Hare Airport, so you could be booking your fun-filled vacation within minutes. Here are some sought-after carriers to check out:

  • Delta
  • United Airlines
  • American Airlines
  • Sun Country Airlines

What is the shortest flight from Brainerd to Chicago?
It can take just 1 hour and 23 minutes to get from MSP to O’Hare Airport. Buckle up and enjoy the ride, because you’ll be landing in a heartbeat.
What airlines fly from Brainerd to Chicago most frequently?
These are the carriers with frequent flights from MSP to ORD. Reserve a seat with one of the following and discover why they are the most sought after: Delta - (DL) with 204 flights every month United Airlines - (UA) with 199 flights every month American Airlines - (AA) with 143 flights every month Sun Country Airlines - (SY) with 17 flights every month
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won’t keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.