$39 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 4 - Thu, May 8
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$222 Roundtrip, found 8 hours ago
$222
Roundtrip
found 8 hours ago
Select Sun Country Airlines flight, departing Sun, May 4 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Thu, May 8, priced at $222 found 8 hours ago
Sun, May 4 - Thu, May 8
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$404 Roundtrip, found 3 days ago
$404
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sun, May 4 from Minneapolis - St. Paul Intl. to Midway Intl., returning Thu, May 8, priced at $404 found 3 days ago

Airfares from $39 One Way, $77 Round Trip from Brainerd to Chicago

Prices starting at $77 for return flights and $39 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.

Mon, Jun 30 - Tue, Jul 1
MSP
Minneapolis
MDW
Chicago
$77 Roundtrip, found 2 days ago
$77
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Mon, Jun 30 from Minneapolis to Chicago, returning Tue, Jul 1, priced at $77 found 2 days ago
Mon, Jun 30 - Tue, Jul 1
MSP
Minneapolis
ORD
Chicago
$77 Roundtrip, found 2 days ago
$77
Roundtrip
found 2 days ago
Select United flight, departing Mon, Jun 30 from Minneapolis to Chicago, returning Tue, Jul 1, priced at $77 found 2 days ago
Mon, Jun 30 - Tue, Jul 1
MSP
Minneapolis
ORD
Chicago
$77 Roundtrip, found 2 days ago
$77
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Jun 30 from Minneapolis to Chicago, returning Tue, Jul 1, priced at $77 found 2 days ago
Wed, Jun 18 - Mon, Jun 23
MSP
Minneapolis
MDW
Chicago
$78 Roundtrip, found 4 days ago
$78
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Jun 18 from Minneapolis to Chicago, returning Mon, Jun 23, priced at $78 found 4 days ago
Tue, May 20 - Wed, May 21
MSP
Minneapolis
ORD
Chicago
$84 Roundtrip, found 3 days ago
$84
Roundtrip
found 3 days ago
Select United flight, departing Tue, May 20 from Minneapolis to Chicago, returning Wed, May 21, priced at $84 found 3 days ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Place Chicago/Hoffman Estates
3.0-star property

Hyatt Place Chicago/Hoffman Estates

8.6/10 Excellent! (1,002 reviews)

Jun 8 - Jun 12

4 night stay

Minneapolis (MSP) to Chicago (ORD)

Denver Air Connection • Non-stop • Coach

Chicago (ORD) to Minneapolis (MSP)

Frontier Airlines • Non-stop • Coach
per person
found 1 day ago
i booked this for my father and he raved about the staff, comfort, and ease of location

Reviewed on May 26, 2024

The Chicago Hotel Collection River North
3.0-star property

The Chicago Hotel Collection River North

7.2/10 Good! (434 reviews)

Jun 8 - Jun 12

4 night stay

Minneapolis (MSP) to Chicago (ORD)

Denver Air Connection • Non-stop • Coach

Chicago (ORD) to Minneapolis (MSP)

Frontier Airlines • Non-stop • Coach
per person
found 1 day ago
The staff is the best!!

Reviewed on Apr 3, 2025

DoubleTree by Hilton Lisle Naperville
4.0-star property

DoubleTree by Hilton Lisle Naperville

7.8/10 Good! (1,001 reviews)

Jun 8 - Jun 12

4 night stay

Minneapolis (MSP) to Chicago (ORD)

Denver Air Connection • Non-stop • Coach

Chicago (ORD) to Minneapolis (MSP)

Frontier Airlines • Non-stop • Coach
per person
found 1 day ago
Clean room and beautiful hotel

Reviewed on Apr 23, 2025

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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

Orbitz can provide you with the greatest deals on a wide range of Brainerd to Chicago flights. Orbitz offers guaranteed low prices and offers you the convenience of cutting-edge mobile tools thus providing you with your best travel experience ever.

Mobile Apps for Brainerd to Chicago Flights

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 Budget Flying Made Simple

Finding cheap flights from Brainerd to Chicago is easy with Orbitz. You can pick and choose airlines for your international flights to create inexpensive yet convenient travel arrangements.

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.